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

HRID 643830Notes

Reaction equation

HRID 643830 reaction equation
[CH3:1][O:2][C:3]([CH:5]1[CH2:9][C:8](=[O:10])[CH:7]=[C:6]1[C:11]([O:13][CH3:14])=[O:12])=[O:4].[BH4-].[Na+]>CO>[CH3:14][O:13][C:11]([CH:6]1[CH2:7][CH:8]([OH:10])[CH:9]=[C:5]1[C:3]([O:2][CH3:1])=[O:4])=[O:12]

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

To a cold solution (−30° C.) of compound 26 (3.18 g, 16.1 mmol) dissolved in MeOH (23 mL), NaBH4 (0.66 g, 17.5 mmol) was added. 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 and 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

Sources & evidence

ORD record
ord-766fa764f74d42e29bf13f48c3178ec6
Source dataset
uspto-grants-2010_04
Patent number
US07700552B2

Reaction notes

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