Ethyl 4-(3,5-bis(trifluoromethyl)benzyloxy)-3-phenyl-2-butenoate → Ethyl 4-(3,5-bis(trifluoromethyl)benzyloxy)-3-phenylbutanoate

HRID 548197Notes

Reaction equation

HRID 548197 reaction equation
[F:1][C:2]([F:30])([F:29])[C:3]1[CH:4]=[C:5]([CH:22]=[C:23]([C:25]([F:28])([F:27])[F:26])[CH:24]=1)[CH2:6][O:7][CH2:8][C:9]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[CH:10][C:11]([O:13][CH2:14][CH3:15])=[O:12].[H][H]>[Pd].[C].C(O)C>[F:1][C:2]([F:29])([F:30])[C:3]1[CH:4]=[C:5]([CH:22]=[C:23]([C:25]([F:27])([F:26])[F:28])[CH:24]=1)[CH2:6][O:7][CH2:8][CH:9]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12]

Participants

5

Reactant 2

HCID 86624036Ethyl 4-(3,5-bis(trifluoromethyl)benzyloxy)-3-phenyl-2-butenoateHCID 178418361HCID 178418361, compound

Product 1

HCID 86624037Ethyl 4-(3,5-bis(trifluoromethyl)benzyloxy)-3-phenylbutanoateYield 100%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

A mixture of ethyl 4-(3,5-bis(trifluoromethyl)benzyloxy)-3-phenyl-2-butenoate (40.00 g, 92.5 mmol), 5% Pd-carbon (1.00 g) and ethanol (250 mL) was stirred for 20 hours at room temperature in a hydrogen atmosphere. After filtering the catalyst, the solvent was evaporated in vacuo to give ethyl 4-(3,5-bis(trifluoromethyl)benzyloxy)-3-phenylbutanoate (40.18 g, 100%) as an oily product. 1H-NMR (DMSO-d6) δ: 1.04 (t, J=7.1 Hz, 3H), 2.60 (dd, J=8.0, 15.5 Hz, 1H), 2.81 (dd, J=6.8, 15.5 Hz, 1H), 3.38-3.45 (m, 1H), 3.65 (d, J=6.9 Hz, 2H), 3.94 (q, J=7.1 Hz, 2H), 4.65 and 4.66 (ABq, J=14.1 Hz, 2H), 7.20-7.24 (m, 1H), 7.28-7.32 (m, 4H), 7.90 (s, 2H), 7.99 (s, 1H).

Workup

  1. filtrationAfter filtering the catalyst
  2. customthe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-58b32a7b63fa40b1b8f88a14aaa20890
Source dataset
uspto-grants-2011_05
Patent number
US07939552B2

Reaction notes

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