p-Anisoyl chloride → HCID 12521848, compound

HRID 1410421Notes

Reaction equation

HRID 1410421 reaction equation
[C:1]([CH:6]=[P:7]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)([O:3][CH2:4][CH3:5])=[O:2].C/C(/O[Si](C)(C)C)=N\[Si](C)(C)C.[C:38](Cl)(=[O:47])[C:39]1[CH:44]=[CH:43][C:42]([O:45][CH3:46])=[CH:41][CH:40]=1>C(Cl)Cl>[CH3:46][O:45][C:42]1[CH:43]=[CH:44][C:39]([C:38](=[O:47])[C:6](=[P:7]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:1]([O:3][CH2:4][CH3:5])=[O:2])=[CH:40][CH:41]=1

Participants

5

Reactant 3

HCID 7477p-Anisoyl chlorideHCID 70670Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl esterHCID 6913588N,O-bis(trimethylsilyl)acetamide

Product 1

HCID 12521848HCID 12521848, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of (carbethoxymethylene)triphenylphosphorane (0.500 g, 1.44 mmol) in DCM (7 ml) under an N2 atmosphere was added N,O-bis(trimethylsilyl)acetamide (0.42 m, 1.7 mmol). The solution was then cooled to 0° C. and p-anisoylchloride (0.250 g, 1.47 mmol) was added. The reaction mixture was then gradually warmed to room temperature and stirred overnight. The reaction was quenched by the addition of H2O (3 ml) and the aqueous phase was extracted with DCM. The combined organic phases were dried over MgSO4 and the solvent removed in vacuo to afford ethyl 3-(4-methoxyphenyl)-3-oxo-2-(triphenylphosphoranylidene)propionate. (0.637 g, 1.32 mmol, 92%) as an off white solid which was used without further purification. 1H NMR (CDCl3) δ 0.62 (3H, t), 3.69 (2H, q), 3.82 (3H, s), 6.86 (2H, d), 7.43-7.55 (9H, m), 7.71-7.80 (8H, m). LCMS (2) Rt: 3.65 min; m/z 483.

Workup

  1. temperatureThe reaction mixture was then gradually warmed to room temperature
  2. customThe reaction was quenched by the addition of H2O (3 ml)
  3. extractionthe aqueous phase was extracted with DCM
  4. dry with materialThe combined organic phases were dried over MgSO4
  5. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-c3154bc29fa249f6b572cfb4fd000d3c
Source dataset
uspto-grants-2014_12
Patent number
US08921544B2

Reaction notes

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