Reaction #4081

ord-a1fa50bc5b0d4b9783d5897925735776

Reaction equation

C=C(C)OC(C)=O
isopropenyl acetate
CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3C=CC4=CC(=O)C=C[C@]4(C)[C@H]3CC[C@]12C
cholesta-1,4,6-trien-3-one
→
CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2C3=CC=C4CC(O)C=C[C@]4(C)[C@H]3CC[C@]12C
cholesta-1,5,7-trien-3-ol
Yield 66.0%

Reactants

C=C(C)OC(C)=O
isopropenyl acetate
—
paratoluenesulfonic acid
CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3C=CC4=CC(=O)C=C[C@]4(C)[C@H]3CC[C@]12C
cholesta-1,4,6-trien-3-one

Reagents

None

Solvents

CCCCOC(C)=O
butyl acetate

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    Temperaturethe resulting mixture was heated
  2. 2
    Temperatureunder reflux for 5 hours
  3. 3
    OtherAfter completion of the reaction

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%.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US04723045uspto-grants-1988_02