Hydrochloric Acid → N-(4-hydroxy-2-butynyl)-2-cyclohexyl-2-hydroxy-2-phenylacetamide
Reaction equation
[OH:1][CH2:2][C:3]#[C:4][CH2:5][NH:6][C:7](=[O:22])[C:8](Cl)([CH:15]1[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.Cl.[O:24]1CCOCC1>>[OH:1][CH2:2][C:3]#[C:4][CH2:5][NH:6][C:7](=[O:22])[C:8]([CH:15]1[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1)([OH:24])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1Participants
4
Conditions
- Temperature
- 90 °C
Procedure
A solution of N-(4-hydroxy-2-butynyl)-2-chloro-2-cyclohexyl-2-phenylacetamide (7.88 g) in a mixture of 1N-hydrochloric acid (85 ml) and 1,4-dioxane (180 ml) was heated at 90° C. for 45 minutes and evaporated in vacuo. To the residue was added water and extracted with ethyl acetate. The extract was washed successively with saturated sodium bicarbonate aqueous solution, water, and sodium chloride aqueous solution, dried over magnesium sulfate, and evaporated in vacuo. The residue was purified by column chromatography on silica gel with a mixture of chloroform and ethyl acetate (5:1) as an eluent to give N-(4-hydroxy-2-butynyl)-2-cyclohexyl-2-hydroxy-2-phenylacetamide as white powder (6.56 g).
Workup
- customevaporated in vacuo
- additionTo the residue was added water
- extractionextracted with ethyl acetate
- washThe extract was washed successively with saturated sodium bicarbonate aqueous solution, water, and sodium chloride aqueous solution
- dry with materialdried over magnesium sulfate
- customevaporated in vacuo
- customThe residue was purified by column chromatography on silica gel with a mixture of chloroform and ethyl acetate (5:1) as an eluent
Sources & evidence
- ORD record
- ord-6ca71073bcc14e47bf9d54a404285a88
- Source dataset
- uspto-grants-1991_11
- Patent number
- US05066680
Reaction notes
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