Methanol → 1-[4-(Benzyloxy)phenyl]-4,4,4-trifluorobutane-1,3-dione

HRID 1003135Notes

Reaction equation

HRID 1003135 reaction equation
[CH3:1][C:2]([C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:6][CH:5]=1)=[O:3].[F:18][C:19]([F:26])([F:25])[C:20](OCC)=[O:21].C[O-].[Na+].CO>CCOCC>[CH2:11]([O:10][C:7]1[CH:8]=[CH:9][C:4]([C:2](=[O:3])[CH2:1][C:20](=[O:21])[C:19]([F:26])([F:25])[F:18])=[CH:5][CH:6]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 9794Ethyl trifluoroacetateHCID 2452261-[4-(Benzyloxy)phenyl]ethan-1-oneHCID 10942334Sodium Methoxide

Product 1

HCID 218944541-[4-(Benzyloxy)phenyl]-4,4,4-trifluorobutane-1,3-dioneYield 96%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of 4-benzyloxyacetophenone (6.50 g, 29 mmol) in ether (70 mL) was cooled to 0° C. and treated with ethyl trifluoroacetate (4.12 g, 29 mmol) and 25% sodium methoxide in methanol (6.39 g, 30 mmol). The reaction was warmed to room temperature and stirred for 64.4 hours. The reaction was quenched with 3 N HCl (15 mL), extracted with ethyl acetate, washed with brine, dried over anhyd. MgSO4, filtered and concentrated in vacuo to give the title compound as a yellow solid (8.91 g, 96%): mp 92.4-96.5° C. 1H NMR (CDCl3) 15.30 (br s, 1 H), 8.86 (d, 2 H, J=8.9 Hz), 7.43 (m, 5 H), 7.08 (d, 2 H, J=8.9 Hz), 6.50 (s, 1 H) 5.16 (s, 2 H).

Workup

  1. customThe reaction was quenched with 3 N HCl (15 mL)
  2. extractionextracted with ethyl acetate
  3. washwashed with brine
  4. customdried over anhyd
  5. filtrationMgSO4, filtered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-88800a8ca56b4159ad864b3e28b051e1
Source dataset
uspto-grants-2000_04
Patent number
US06045773

Reaction notes

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