Triphenylphosphine → Ethyl 2-(triphenylphosphoranylidene)propionate

HRID 1296852Notes

Reaction equation

HRID 1296852 reaction equation
[C:1]1([P:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[CH:21]([CH3:27])[C:22]([O:24][CH2:25][CH3:26])=[O:23]>C(OCC)(=O)C>[CH2:25]([O:24][C:22](=[O:23])[C:21](=[P:7]([C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)[CH3:27])[CH3:26]

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 79040Ethyl 2-bromopropionate

Product 1

HCID 79792Ethyl 2-(triphenylphosphoranylidene)propionateYield 75%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

1.6 Kg (6.10 mol) triphenyl phosphine was dissolved in 10 L ethyl acetate and 1.0 Kg of ethyl 2-bromopropionate was added into the above solution. The reaction mixture was stirred at room temperature for 2 days. White solid was filtered off and the precipitate was washed with ethyl acetate. The resulting compound was dissolved in methanol and treated with saturated aqueous potassium carbonate. After stirring for 2 h, the yellow solid was filtered off and washed with water to give 1.5 Kg (75%) of desired product.

Workup

  1. filtrationWhite solid was filtered off
  2. washthe precipitate was washed with ethyl acetate
  3. dissolutionThe resulting compound was dissolved in methanol
  4. additiontreated with saturated aqueous potassium carbonate
  5. stirringAfter stirring for 2 h
  6. filtrationthe yellow solid was filtered off
  7. washwashed with water

Sources & evidence

ORD record
ord-091447b518594d91a10a684c767f957c
Source dataset
uspto-grants-2007_07
Patent number
US07247752B2

Reaction notes

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