Ethyl Acetate → HCID 14742618, compound

HRID 1662362Notes

Reaction equation

HRID 1662362 reaction equation
[C:1]([CH2:6][CH:7]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([O:3][CH2:4][CH3:5])=[O:2].[CH2:27]([O:34][C:35]1[CH:36]=[C:37]([CH:40]=[CH:41][CH:42]=1)[CH:38]=O)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.CCOC(C)=O>C1COCC1>[CH2:27]([O:34][C:35]1[CH:36]=[C:37](/[CH:38]=[C:6](\[CH3:7])/[C:1]([O:3][CH2:4][CH3:5])=[O:2])[CH:40]=[CH:41][CH:42]=1)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 743423-BenzyloxybenzaldehydeHCID 12607919Ethyl 3-(triphenyl-lambda~5~-phosphanylidene)propanoate

Product 1

HCID 14742618HCID 14742618, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of (carbethoxyethylidene)triphenylphosphorane (available from Aldrich) (5.50 g, 15.2 mmol) in THF (25 mL) was added 3-(benzyloxy)benzaldehyde (available from Aldrich) (2.93 g, 13.8 mmol) in THF (10 mL) under nitrogen at −78° C. The reaction was allowed to slowly warm to room temperature and stirred for 2 hours. EtOAc (100 mL) was added, and the mixture was washed with brine (30×2 mL). The organic layer was dried over MgSO4. The solvent was removed by evaporation. The crude product was purified by passing through a short silica gel column, eluting with hexane/EtOAc (85/15) to give (E)-ethyl 3-(3-(benzyloxy)phenyl)-2-methylacrylate 62.B.

Workup

  1. washthe mixture was washed with brine (30×2 mL)
  2. dry with materialThe organic layer was dried over MgSO4
  3. customThe solvent was removed by evaporation
  4. customThe crude product was purified
  5. washeluting with hexane/EtOAc (85/15)

Sources & evidence

ORD record
ord-7d61385a5f96476783b35daa28acd8b0
Source dataset
uspto-grants-2011_10
Patent number
US08030354B2

Reaction notes

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