Sodium borohydride → Methyl 2-hydroxy-3-methylcyclopentanecarboxylate

HRID 58821Notes

Reaction equation

HRID 58821 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

HCID 4311764Sodium borohydrideHCID 47381223-Methyl-2-oxocyclopentanecarboxylic acid methyl ester

Product 1

HCID 117608075Methyl 2-hydroxy-3-methylcyclopentanecarboxylateYield 82.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

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

  1. customThe reaction was quenched with saturated aqueous NH4Cl (500 mL)
  2. extractionthe resulting mixture was extracted with EtOAc (250 mL×5)
  3. washThe combined organic phases were washed with brine (500 mL×2)
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-bb6b442ebf30401cb31e8a2f50cf7998
Source dataset
uspto-grants-2016_09
Patent number
US09434761B2

Reaction notes

Loading…