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

HRID 1443445Notes

Reaction equation

HRID 1443445 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 61 (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 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-608bf57d45a34957bceb7569810fbf6e
Source dataset
uspto-grants-2010_02
Patent number
US07659245B2

Reaction notes

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