Isopropenyl acetate → Cholesta-1,5,7-trien-3-ol

HRID 3985

Reaction equation

HRID 3985 reaction equation
[CH3:1][CH:2]([CH2:4][CH2:5][CH2:6][C@H:7]([C@@H:9]1[C@:26]2([CH3:27])[C@H:12]([C@H:13]3[C@H:23]([CH2:24][CH2:25]2)[C@:21]2([CH3:22])[C:16](=[CH:17][C:18](=[O:28])[CH:19]=[CH:20]2)[CH:15]=[CH:14]3)[CH2:11][CH2:10]1)[CH3:8])[CH3:3].C(OC(C)=C)(=O)C>C(OCCCC)(=O)C>[CH3:3][CH:2]([CH2:4][CH2:5][CH2:6][C@H:7]([C@@H:9]1[C@:26]2([CH3:27])[C@H:12]([C:13]3[C@H:23]([CH2:24][CH2:25]2)[C@:21]2([CH3:22])[C:16]([CH2:17][CH:18]([OH:28])[CH:19]=[CH:20]2)=[CH:15][CH:14]=3)[CH2:11][CH2:10]1)[CH3:8])[CH3:1]

Participants

4

Reactant 2

HCID 7916Isopropenyl acetateHCID 1073901,4,6-Cholestatrien-3-one

Product 1

HCID 18611553Cholesta-1,5,7-trien-3-olYield 66%

Reagents, catalysts & solvents 1

HCID 31272Butyl AcetateSolvent

Procedure

To a mixture of 38 g (0.1 mol) of cholesta-1,4,6-trien-3-one (I) and 34 g (0.2 mol) of paratoluenesulfonic acid were added 200 ml of butyl acetate and further 200 g (2 mol) of isopropenyl acetate, and the resulting mixture was heated under reflux for 5 hours. After completion of the reaction, the same treatment as in Example 1 was carried out to yield 25.2 g of cholesta-1,5,7-trien-3-ol (IV). The yield was 66%.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureunder reflux for 5 hours
  3. customAfter completion of the reaction

Sources & evidence

ORD record
ord-a1fa50bc5b0d4b9783d5897925735776
Source dataset
uspto-grants-1988_02
Patent number
US04723045

Linked notes

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