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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1443445Generated: October 31, 2026

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

https://huagongshe.com/reaction/1443445

Reaction equation

Participants

RoleNameHCIDCharge
ReactantSodium borohydrideHCID 4311764—
Reactant1,2-Dimethyl 4-oxo-2-cyclopentene-1,2-dicarboxylateHCID 59165463—
SolventMethanolHCID 887—
Product4-Hydroxy-cyclopent-2-ene-1,2-dicarboxylic acid dimethyl esterHCID 5916544393.1%

Reaction Steps

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.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07659245B2
Source datasetuspto-grants-2010_02
ORD IDord-608bf57d45a34957bceb7569810fbf6e
Source noteuspto-grants-2010_02