Borane → Methyl 3-tert-butyl-5-(hydroxymethyl)benzoate
Reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH:11]=[C:12]([C:14]([O:16][CH3:17])=[O:15])[CH:13]=1)[C:8](O)=[O:9])([CH3:4])([CH3:3])[CH3:2].B>C1COCC1>[C:1]([C:5]1[CH:13]=[C:12]([CH:11]=[C:7]([CH2:8][OH:9])[CH:6]=1)[C:14]([O:16][CH3:17])=[O:15])([CH3:4])([CH3:2])[CH3:3]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 50 °C
Procedure
To a solution of 3-tert-butyl-5-(methoxycarbonyl)benzoic acid (8.66 g, 0.0293 mol) in THF (60 mL) was slowly added borane-dimethyl sulfide complex (7.8 mL, 0.088 mol) over 20 min at rt. The reaction mixture was heated at 50° C. for 2 h. An additional amount of borane-dimethyl sulfide complex (7.8 mL, 0.088 mol) was added to reaction mixture and the heat increased to 80° C. The reaction mixture was allowed to stir for an additional 2 h. Unreacted borane was quenched by the addition of MeOH. Water was added and the mixture was extracted with EtOAc. The organic solutions were combined, washed with brine, dried over MgSO4, filtered and concentrated. The residue was purified by column chromatography and triturated to give methyl 3-tert-butyl-5-(hydroxymethyl)benzoate (3.0 g, 46%) as a white solid. LCMS ES+ 223.
Workup
- customover 20 min
- customat rt
- additionAn additional amount of borane-dimethyl sulfide complex (7.8 mL, 0.088 mol) was added to reaction mixture
- temperaturethe heat increased to 80° C
- customwas quenched by the addition of MeOH
- additionWater was added
- extractionthe mixture was extracted with EtOAc
- washwashed with brine
- dry with materialdried over MgSO4
- filtrationfiltered
- concentrationconcentrated
- customThe residue was purified by column chromatography
- customtriturated
Sources & evidence
- ORD record
- ord-a2210f663b94451f9344e8fad72eaccf
- Source dataset
- uspto-grants-2012_02
- Patent number
- US08110687B2
Reaction notes
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