Sodium borohydride → 2-Methoxycarbonyl-3-methoxycarbonylmethyl-2-(cis-2-pentenyl)-cyclopentanol

HRID 46551Notes

Reaction equation

HRID 46551 reaction equation
[C:1]([O:5][C:6]([C:8]1([CH2:19]/[CH:20]=[CH:21]\[CH2:22][CH3:23])[C:12](=[O:13])[CH:11]=[CH:10][CH:9]1[CH2:14][C:15]([O:17][CH3:18])=[O:16])=[O:7])(C)(C)C.[BH4-].[Na+]>CO>[CH3:1][O:5][C:6]([C:8]1([CH2:19]/[CH:20]=[CH:21]\[CH2:22][CH3:23])[CH:9]([CH2:14][C:15]([O:17][CH3:18])=[O:16])[CH2:10][CH2:11][CH:12]1[OH:13])=[O:7]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 70583183HCID 70583183, compound2×

Product 1

HCID 706010102-Methoxycarbonyl-3-methoxycarbonylmethyl-2-(cis-2-pentenyl)-cyclopentanol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A 220 mg quantity of 5-methoxycarbonyl-4-methoxycarbonylmethyl-5-(cis-2-pentenyl)-2-cyclopentenone (compound (2-b)) and 60 mg of sodium borohydride are dissolved in 50 ml of methanol, and the solution is refluxed for one hour. The same procedure as in Example 1 is thereafter repeated, affording 2-methoxycarbonyl-3-methoxycarbonylmethyl-2-(cis-2-pentenyl)-cyclopentanol (compound (1-b), R1 =R2 =CH3) in a yield of 94.7%, b.p. 74°-78° C./0.01 mm Hg.

Workup

  1. temperaturethe solution is refluxed for one hour

Sources & evidence

ORD record
ord-c5282019786c43e2ad0bdcea505c5eb3
Source dataset
uspto-grants-1979_11
Patent number
US04173707

Reaction notes

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