Sodium borohydride → 4-Hydroxy-cyclopent-2-ene-1,2-dicarboxylic acid dimethyl ester

HRID 1429190Notes

Reaction equation

HRID 1429190 reaction equation
[BH4-].[Na+].[CH3:3][O:4][C:5]([CH:7]1[CH2:11][C:10](=[O:12])[CH:9]=[C:8]1[C:13]([O:15][CH3:16])=[O:14])=[O:6]>CO>[CH3:16][O:15][C:13]([CH:8]1[CH2:9][CH:10]([OH:12])[CH:11]=[C:7]1[C:5]([O:4][CH3:3])=[O:6])=[O:14]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 591654631,2-Dimethyl 4-oxo-2-cyclopentene-1,2-dicarboxylate

Product 1

HCID 591654434-Hydroxy-cyclopent-2-ene-1,2-dicarboxylic acid dimethyl esterYield 93.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

NaBH4 (0.66 g, 17.5 mmol) dissolved in MeOH (23 mL) was added to a cold solution (−30° C.) of the ketone 23a (3.18 g, 16.1 mmol). After nine minutes the excess of NaBH4 was destroyed by adding brine (80 mL). The mixture was concentrated and extracted with ethyl acetate (4×80 ml). The organic phases were dried, filtrated and concentrated which gave the title compound (3.0 g, 92%) as a yellow oil.

Workup

  1. customAfter nine minutes the excess of NaBH4 was destroyed
  2. additionby adding brine (80 mL)
  3. concentrationThe mixture was concentrated
  4. extractionextracted with ethyl acetate (4×80 ml)
  5. customThe organic phases were dried
  6. filtrationfiltrated
  7. concentrationconcentrated which

Sources & evidence

ORD record
ord-12facf2eb21845baa7e9cba33c1b1533
Source dataset
uspto-grants-2015_01
Patent number
US08937080B2

Reaction notes

Loading…