methyl 3-[(2S)-1-(difluoromethoxy)propan-2-yl]oxy-5-phenylmethoxy-benzoate → methyl 3-[(2S)-1-(difluoromethoxy)propan-2-yl]oxy-5-hydroxy-benzoate
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
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Procedure
Methyl 3-({(1S)-2-[(difluoromethyl)oxy]-1-methylethyl}oxy)-5-[(phenylmethyl)oxy]benzoate (0.48 g, 1.08 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 as a colourless oil (1.05 g). 1H NMR δ (CDCl3): 1.35 (d, 3H), 3.90 (s, 3H), 3.90-4.02 (m, 2H), 4.57-4.64 (m, 1H), 5.20 (s, 1H), 6.26 (t, 1H), 6.63 (t, 1H), 7.14-7.15 (m, 1H), 7.17-7.18 (m, 1H); m/z 275 (M−H)−
Workup
- customTHF (10 mL) and the flask evacuated
- custompurged with argon (3 times)
- addition10% Palladium on carbon (140 mg) was added
- customthe flask further evacuated
- customfinally purged with hydrogen gas
- customThe reaction mixture was evacuated
- custompurged with argon (3 times)
- customthe catalyst removed by filtration through Celite®
- concentrationThe filtrate was concentrated in vacuo
Sources & evidence
- ORD record
- ord-672a75fc78d94b4ebf30e333e66e1a27
- Source dataset
- uspto-grants-2010_01
- Patent number
- US07642259B2
Reaction notes
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