Water → 4-Hydroxy-3-methyl-2-(prop-2-yn-1-yl)cyclopent-2-en-1-one

HRID 1583501Notes

Reaction equation

HRID 1583501 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][C:13]#[CH:14].O>C(Cl)(Cl)Cl>[OH:7][C@H:6]1[CH2:5][C:4](=[O:11])[C:3]([CH2:12][C:13]#[CH:14])=[C:2]1[CH3:1]

Participants

4

Reactant 2

HCID 962WaterHCID 13387529(R)-3-methyl-4-nitroxy-2-(2-propynyl)-2-cyclopenten-1-one

Product 1

HCID 1569974-Hydroxy-3-methyl-2-(prop-2-yn-1-yl)cyclopent-2-en-1-oneYield 90%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A mixture of 1.95 g of crude (R)-3-methyl-4-nitroxy-2-(2-propynyl)-2-cyclopenten-1-one and 30 ml of water was stirred at a temperature of 85°-90° C. for 4 hours. Thereafter, with the same operations as in Example 3, 1.35 g of (S)-4-hydroxy-3-methyl-2-(2-propynyl)-2-cyclopenten-1-one (chemical purity: 90.2%, [α]D24 : +13.1° (C=1.07, in chloroform), (R)-isomer/(S)-isomer=16.2/83.8) was obtained.

Sources & evidence

ORD record
ord-b48e388f976746f49ad658e58421bdf2
Source dataset
uspto-grants-1985_11
Patent number
US04552703

Reaction notes

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