p-Toluenesulfonic acid → HCID 53969888, compound

HRID 1981876Notes

Reaction equation

HRID 1981876 reaction equation
[C:1]([O:4][C@H:5]1[CH:29]2[C@:24](C)([CH2:25]CC(=O)[CH2:28]2)[C@@H:23]2[C@H:7]([C@H:8]3[C@:20]([CH3:32])([CH2:21][CH2:22]2)[C@@H:11]([C@H:12]([CH3:19])[CH2:13][CH2:14][CH2:15][CH:16]([CH3:18])[CH3:17])[CH2:10][CH2:9]3)[CH2:6]1)(=[O:3])[CH3:2].[C:33]([O:36][C:37]([CH3:39])=[CH2:38])(=[O:35])[CH3:34].C1(C)C=CC(S(O)(=O)=O)=CC=1>>[C:33]([O:36][C:37]1[CH2:39][C@@:24]2([CH3:25])[CH:29]([C@H:5]([O:4][C:1](=[O:3])[CH3:2])[CH2:6][C@@H:7]3[C@@H:23]2[CH2:22][CH2:21][C@@:20]2([CH3:32])[C@H:8]3[CH2:9][CH2:10][C@@H:11]2[C@H:12]([CH3:19])[CH2:13][CH2:14][CH2:15][CH:16]([CH3:17])[CH3:18])[CH2:28][CH:38]=1)(=[O:35])[CH3:34]

Participants

4

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 7916Isopropenyl acetateHCID 13686441HCID 13686441, compound

Product 1

HCID 53969888HCID 53969888, compoundYield 95%

Procedure

A solution of 6β-acetoxycholestan-3-one (1) (1215 mg, 2.74 mmol) of isopropenyl acetate (15 ml) was refluxed in the presence of ρ-toluenesulfonic acid (20 mg) under argon for 3 hr. Most of the solvent was removed and the concentrated mixture was extracted with ethyl acetate. The extract was washed with saturated NaHCO3, and brine, and dried over MgSO4. The residue obtained upon evaporation of the solvent was purified by column chromatography on silica gel (40 g). Elution with benzene gave the enol-acetate (2) (1265 mg, 95%), glass; δ0.71(3H, s, 18-H3), 0.88(6H, d, J=6 Hz, 26- and 27-H3), 0.91(3H, d, J=6 Hz, 21-H3), 1.02(3H, s, 19-H3) 1.08 and 1.11 (6H, Sx2, 2- and 6-acetyl), 5.03(1H, m, 6α-H), and 5.23(1H, dd, J=5 and 2 Hz).

Workup

  1. customMost of the solvent was removed
  2. extractionthe concentrated mixture was extracted with ethyl acetate
  3. washThe extract was washed with saturated NaHCO3, and brine
  4. dry with materialdried over MgSO4
  5. customThe residue obtained upon evaporation of the solvent
  6. customwas purified by column chromatography on silica gel (40 g)
  7. washElution with benzene

Sources & evidence

ORD record
ord-53ac8645905a48eb94d30f48e009f0dd
Source dataset
uspto-grants-1986_06
Patent number
US04594192

Reaction notes

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