Sodium borohydride → Methyl 2-hydroxy-3-methylcyclopentanecarboxylate
Reaction equation
[BH4-].[Na+].[CH3:3][CH:4]1[CH2:8][CH2:7][CH:6]([C:9]([O:11][CH3:12])=[O:10])[C:5]1=[O:13]>CO>[OH:13][CH:5]1[CH:4]([CH3:3])[CH2:8][CH2:7][CH:6]1[C:9]([O:11][CH3:12])=[O:10]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
NaBH4 (9.98 g, 0.260 mol) was added in portions to a solution of methyl 3-methyl-2-oxocyclopentanecarboxylate (41.2 g, 0.26 mol) in MeOH (250 mL) at 0° C. The reaction mixture was allowed to warm to ambient temperature and stirred for 5 h. The reaction was quenched with saturated aqueous NH4Cl (500 mL) and the resulting mixture was extracted with EtOAc (250 mL×5). The combined organic phases were washed with brine (500 mL×2), dried over anhydrous sodium sulfate, and concentrated to afford methyl 2-hydroxy-3-methylcyclopentanecarboxylate (34.0 g).
Workup
- customThe reaction was quenched with saturated aqueous NH4Cl (500 mL)
- extractionthe resulting mixture was extracted with EtOAc (250 mL×5)
- washThe combined organic phases were washed with brine (500 mL×2)
- dry with materialdried over anhydrous sodium sulfate
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-bb6b442ebf30401cb31e8a2f50cf7998
- Source dataset
- uspto-grants-2016_09
- Patent number
- US09434761B2
Reaction notes
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