Water → (R)-4-hydroxy-3-methyl-2-(2-propenyl)-2-cyclopenten-1-one

HRID 1583503Notes

Reaction equation

HRID 1583503 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 13535752HCID 13535752, compound

Product 1

HCID 12225759(R)-4-hydroxy-3-methyl-2-(2-propenyl)-2-cyclopenten-1-oneYield 94.2%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A mixture of 0.99 g of purified (S)-3-methyl-4-nitroxy-2-(2-propenyl)-2-cyclopenten-1-one prepared in Example 6, 0.50 g of calcium carbonate and 30 ml of water was stirred at a temperature of 85°-90° C. for 2 hours. Thereafter, with the same operations as in Example 3, 0.72 g of (R)-4-hydroxy-3-methyl-2-(2-propenyl)-2-cyclopenten-1-one (chemical purity: 94.2%, [α]D24 : -6.64° (C=1.18, in chloroform), (R)-isomer/(S)-isomer=76.2/23.8) was obtained.

Sources & evidence

ORD record
ord-e721efd490c541638b585df8a4fe5466
Source dataset
uspto-grants-1985_11
Patent number
US04552703

Reaction notes

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