methyl 3-[(2S)-1-(difluoromethoxy)propan-2-yl]oxy-5-phenylmethoxy-benzoate → methyl 3-[(2S)-1-(difluoromethoxy)propan-2-yl]oxy-5-hydroxy-benzoate

HRID 2241946Notes

Reaction equation

HRID 2241946 reaction equation
[F:1][CH:2]([F:26])[O:3][CH2:4][C@@H:5]([O:7][C:8]1[CH:9]=[C:10]([CH:15]=[C:16]([O:18]CC2C=CC=CC=2)[CH:17]=1)[C:11]([O:13][CH3:14])=[O:12])[CH3:6]>C(O)C>[F:1][CH:2]([F:26])[O:3][CH2:4][C@@H:5]([O:7][C:8]1[CH:9]=[C:10]([CH:15]=[C:16]([OH:18])[CH:17]=1)[C:11]([O:13][CH3:14])=[O:12])[CH3:6]

Participants

3

Reactant 1

HCID 59127143methyl 3-[(2S)-1-(difluoromethoxy)propan-2-yl]oxy-5-phenylmethoxy-benzoate

Product 1

HCID 59127138methyl 3-[(2S)-1-(difluoromethoxy)propan-2-yl]oxy-5-hydroxy-benzoateYield 345.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Methyl 3-[(2S)-1-(difluoromethoxy)propan-2-yl]oxy-5-phenylmethoxy-benzoate (0.48 g, 1.1 mmol) was dissolved in ethanol (10 mL) and THF (10 mL) and the flask evacuated and purged with argon (3 times). 10% Palladium on carbon (140 mg) was added and the flask further evacuated and finally purged with hydrogen gas. The reaction mixture was stirred at RT for 20 hours until completion. The reaction mixture was evacuated and purged with argon (3 times) then the catalyst removed by filtration through Celite®. The filtrate was concentrated in vacuo to give the desired compound (1.05 g).

Workup

  1. customTHF (10 mL) and the flask evacuated
  2. custompurged with argon (3 times)
  3. addition10% Palladium on carbon (140 mg) was added
  4. customthe flask further evacuated
  5. customfinally purged with hydrogen gas
  6. customThe reaction mixture was evacuated
  7. custompurged with argon (3 times)
  8. customthe catalyst removed by filtration through Celite®
  9. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-7a794d1dcaf34e9790fa7eb271722f27
Source dataset
uspto-grants-2010_03
Patent number
US07671060B2

Reaction notes

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