Water → (4S)-Hydroxy-3-methyl-2-(2-propenyl)-2-cyclopentene-1-one

HRID 1583506Notes

Reaction equation

HRID 1583506 reaction equation
[CH3:1][C:2]1[C@H:6]([O:7][N+]([O-])=O)[CH2:5][C:4](=[O:11])[C:3]=1[CH2:12][CH:13]=[CH2:14].C(=O)([O-])[O-].[Ca+2].O>C(Cl)(Cl)Cl>[OH:7][C@H:6]1[CH2:5][C:4](=[O:11])[C:3]([CH2:12][CH:13]=[CH2:14])=[C:2]1[CH3:1]

Participants

5

Reactant 3

HCID 962WaterHCID 10112Calcium CarbonateHCID 13535751HCID 13535751, compound

Product 1

HCID 12225760(4S)-Hydroxy-3-methyl-2-(2-propenyl)-2-cyclopentene-1-oneYield 78.9%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A mixture of 1.97 g of (R)-3-methyl-4-nitroxy-2-(2-propenyl)-2-cyclopenten-1-one prepared in Example 10, 0.20 g of calcium carbonate and 30 ml of water was stirred at 85°-90° C. for 3 hours. Thereafter, with the same operations as in Example 3, 1.20 g of (S)-4-hydroxy-3-methyl-2-(2-propenyl)-2-cyclopenten-1-one (chemical purity: 93.6%, [α]D24 : +11.2° (C=1.23, in chloroform), (R)-isomer/(S)-isomer=14.8/85.2) was obtained.

Sources & evidence

ORD record
ord-23df0b488d954312a3e85aeff110c116
Source dataset
uspto-grants-1985_11
Patent number
US04552703

Reaction notes

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