Ethyl Acetate → (E)-Ethyl 3-(4-(benzyloxy)phenyl)-2-methylacrylate

HRID 2101761Notes

Reaction equation

HRID 2101761 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:42]=[CH:41][C:38]([CH:39]=O)=[CH:37][CH:36]=1)[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:42]=[CH:41][C:38](/[CH:39]=[C:6](\[CH3:7])/[C:1]([O:3][CH2:4][CH3:5])=[O:2])=[CH:37][CH:36]=1)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 78109Benzaldehyde, 4-(phenylmethoxy)-HCID 12607919Ethyl 3-(triphenyl-lambda~5~-phosphanylidene)propanoate

Product 1

HCID 12235562(E)-Ethyl 3-(4-(benzyloxy)phenyl)-2-methylacrylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of (carbethoxyethylidene)triphenylphosphorane (5.50 g, 15.2 mmol) (commercially available from Aldrich, catalog #377708) in THF (25 mL) was added 4-(benzyloxy)benzaldehyde (12.1) (2.93 g, 13.8 mmol) (commercially available from Lancaster, catalog #6285) 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 the title compound. 1H NMR (CDCl3) δ 7.65 (s, 1H), 7.46-7.35 (m, 7H), 7.01 (d, 2H), 5.11(s, 2H), 4.28 (q, 2H), 2.14 (s, 3H), 1.36 (t, 3H).

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-34e6f525555d4f06bf5333a1389f2f9a
Source dataset
uspto-grants-2009_08
Patent number
US07572934B2

Reaction notes

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