Triphenylphosphine → Ethyl 2-(triphenylphosphoranylidene)propionate

HRID 2115627Notes

Reaction equation

HRID 2115627 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-3fcc9660264e44e4aea9f3469d92dabc
Source dataset
uspto-grants-2008_10
Patent number
US07435861B2

Reaction notes

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