Knowledge (XXG)

Triethyl phosphonoacetate

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solution to prepare a phosphonate anion. It has an acidic proton that can easily be abstracted by a weak base. When used in an HWE reaction with a carbonyl the resulting alkene formed is usually the
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Rathke, Michael W.; Nowak, Michael (July 1985). "The Horner-Wadsworth-Emmons modification of the Wittig reaction using triethylamine and lithium or magnesium salts".
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142 to 145 °C (288 to 293 °F; 415 to 418 K) at 9 mmHg
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Except where otherwise noted, data are given for materials in their
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InChI=1S/C8H17O5P/c1-4-11-8(9)7-14(10,12-5-2)13-6-3/h4-7H2,1-3H3
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InChI=1/C8H17O5P/c1-4-11-8(9)7-14(10,12-5-2)13-6-3/h4-7H2,1-3H3
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alkene, and is generated with excellent regioselectivity.
553: 340: 424:. Unsourced material may be challenged and removed. 378:Triethyl phosphonoacetate can be added dropwise to 151: 63: 573: 8: 580: 566: 204: 129: 107: 15: 484:Learn how and when to remove this message 375:(HWE) or the Horner-Emmons modification. 171: 497: 260: 225: 200: 120: 232:Key: GGUBFICZYGKNTD-UHFFFAOYSA-N 7: 534: 532: 422:adding citations to reliable sources 242:Key: GGUBFICZYGKNTD-UHFFFAOYAB 142: 552:. You can help Knowledge (XXG) by 14: 41:Ethyl (diethoxyphosphoryl)acetate 536: 507:The Journal of Organic Chemistry 398: 373:Horner-Wadsworth-Emmons reaction 330: 22: 409:needs additional citations for 326:(at 25 °C , 100 kPa). 604:Reagents for organic chemistry 1: 433:"Triethyl phosphonoacetate" 630: 531: 306:224.19 g/mol 17:Triethyl phosphonoacetate 365:Triethyl phosphonoacetate 320: 271: 251: 216: 47: 35: 30: 21: 614:Organic compound stubs 544:This article about an 263:CCOC(=O)CP(=O)(OCC)OCC 418:improve this article 37:Preferred IUPAC name 519:10.1021/jo00215a004 18: 599:Phosphonate esters 353:Infobox references 16: 561: 560: 513:(15): 2624–2626. 494: 493: 486: 468: 369:organic synthesis 367:is a reagent for 361:Chemical compound 359: 358: 185:CompTox Dashboard 89:Interactive image 621: 582: 575: 568: 546:organic compound 540: 533: 523: 522: 502: 489: 482: 478: 475: 469: 467: 426: 402: 394: 380:sodium methoxide 343: 337: 334: 333: 279:Chemical formula 209: 208: 193: 191: 175: 155: 144: 133: 122: 111: 91: 67: 26: 19: 629: 628: 624: 623: 622: 620: 619: 618: 589: 588: 587: 586: 529: 527: 526: 504: 503: 499: 490: 479: 473: 470: 427: 425: 415: 403: 392: 362: 355: 350: 349: 348:  ?) 339: 335: 331: 327: 295: 291: 287: 281: 267: 264: 259: 258: 247: 244: 243: 240: 234: 233: 230: 224: 223: 212: 194: 187: 178: 158: 145: 114: 94: 81: 70: 57: 43: 42: 12: 11: 5: 627: 625: 617: 616: 611: 606: 601: 591: 590: 585: 584: 577: 570: 562: 559: 558: 541: 525: 524: 496: 495: 492: 491: 406: 404: 397: 391: 388: 360: 357: 356: 351: 329: 328: 324:standard state 321: 318: 317: 314: 308: 307: 304: 298: 297: 293: 289: 285: 282: 277: 274: 273: 269: 268: 266: 265: 262: 254: 253: 252: 249: 248: 246: 245: 241: 238: 237: 235: 231: 228: 227: 219: 218: 217: 214: 213: 211: 210: 197: 195: 183: 180: 179: 177: 176: 168: 166: 160: 159: 157: 156: 148: 146: 138: 135: 134: 124: 116: 115: 113: 112: 104: 102: 96: 95: 93: 92: 84: 82: 75: 72: 71: 69: 68: 60: 58: 53: 50: 49: 45: 44: 40: 39: 33: 32: 28: 27: 13: 10: 9: 6: 4: 3: 2: 626: 615: 612: 610: 607: 605: 602: 600: 597: 596: 594: 583: 578: 576: 571: 569: 564: 563: 557: 555: 551: 547: 542: 539: 535: 530: 520: 516: 512: 508: 501: 498: 488: 485: 477: 466: 463: 459: 456: 452: 449: 445: 442: 438: 435: –  434: 430: 429:Find sources: 423: 419: 413: 412: 407:This article 405: 401: 396: 395: 389: 387: 385: 381: 376: 374: 370: 366: 354: 347: 342: 325: 319: 315: 313: 312:Boiling point 310: 309: 305: 303: 300: 299: 283: 280: 276: 275: 270: 261: 257: 250: 236: 226: 222: 215: 207: 203: 202:DTXSID4041573 199: 198: 196: 186: 182: 181: 174: 170: 169: 167: 165: 162: 161: 154: 150: 149: 147: 141: 137: 136: 132: 128: 125: 123: 121:ECHA InfoCard 118: 117: 110: 106: 105: 103: 101: 98: 97: 90: 86: 85: 83: 79: 74: 73: 66: 62: 61: 59: 56: 52: 51: 46: 38: 34: 29: 25: 20: 609:Ethyl esters 554:expanding it 543: 528: 510: 506: 500: 480: 471: 461: 454: 447: 440: 428: 416:Please help 411:verification 408: 383: 377: 371:used in the 364: 363: 48:Identifiers 272:Properties 127:100.011.598 593:Categories 474:March 2014 444:newspapers 390:References 302:Molar mass 173:022826171T 100:ChemSpider 76:3D model ( 55:CAS Number 296:P 65:867-13-0 458:scholar 346:what is 344: ( 140:PubChem 460:  453:  446:  439:  431:  341:verify 338:  256:SMILES 31:Names 548:is a 465:JSTOR 451:books 221:InChI 153:13345 109:12776 78:JSmol 550:stub 437:news 164:UNII 515:doi 420:by 190:EPA 143:CID 595:: 511:50 509:. 290:17 581:e 574:t 567:v 556:. 521:. 517:: 487:) 481:( 476:) 472:( 462:· 455:· 448:· 441:· 414:. 384:E 336:N 294:5 292:O 288:H 286:8 284:C 192:) 188:( 80:)

Index


Preferred IUPAC name
CAS Number
867-13-0
JSmol
Interactive image
ChemSpider
12776
ECHA InfoCard
100.011.598
Edit this at Wikidata
PubChem
13345
UNII
022826171T
CompTox Dashboard
DTXSID4041573
Edit this at Wikidata
InChI
SMILES
Chemical formula
Molar mass
Boiling point
standard state
verify
what is
Infobox references
organic synthesis
Horner-Wadsworth-Emmons reaction
sodium methoxide

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