Potassium Hydroxide → 13-(2-Chlorovinyl)-10-methyl-gon-5-ene-3beta,17beta-diol
Reaction equation
[OH-].[K+].C([O:6][C@H:7]1[CH2:30][CH2:29][C@@:28]2([CH3:31])[C:9](=[CH:10][CH2:11][C@H:12]3[C@H:20]4[C@@:16]([CH:25]=[CH:26][Cl:27])([C@@H:17]([O:21]C(=O)C)[CH2:18][CH2:19]4)[CH2:15][CH2:14][C@@H:13]32)[CH2:8]1)(=O)C>CO>[Cl:27][CH:26]=[CH:25][C@:16]12[CH2:15][CH2:14][C@@H:13]3[C@:28]4([CH3:31])[C:9](=[CH:10][CH2:11][C@H:12]3[C@@H:20]1[CH2:19][CH2:18][C@@H:17]2[OH:21])[CH2:8][C@@H:7]([OH:6])[CH2:30][CH2:29]4Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 45 °C
Procedure
After adding 66 ml of a 10% strength aqueous potassium hydroxide solution, a solution of 1.68 g of 3β,17β-diacetoxy-13-(2-chlorovinyl)-10-methyl-gon-5-ene (a mixture of the cis and trans isomers in a ratio of 1:3) in 132 ml of methanol is stirred for 90 minutes at 45° C whilst passing nitrogen through the mixture. The reaction mixture is then concentrated to about 40 ml in a water pump vacuum and taken up in ethyl acetate. The organic phase, which is separated off, is washed with 1 N hydrochloric acid and with water until neutral, dried and evaporated. Chromatography on silica gel using a mixture of hexane/ethyl acetate (2:1) as the eluant gives 13-(2-chlorovinyl)-10-methyl-gon-5-ene-3β,17β-diol (a corresponding mixture of the cis and trans isomers) in an amorphous form.
Workup
- concentrationThe reaction mixture is then concentrated to about 40 ml in a water pump vacuum
- customThe organic phase, which is separated off
- washis washed with 1 N hydrochloric acid and with water until neutral,
- customdried
- customevaporated
- additionChromatography on silica gel using a mixture of hexane/ethyl acetate (2:1) as the eluant
Sources & evidence
- ORD record
- ord-0c343c85d4a348dab80db3a03b230331
- Source dataset
- uspto-grants-1977_10
- Patent number
- US04052421
Reaction notes
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