Hydrochloric Acid → HCID 9932250, compound

HRID 1816483Notes

Reaction equation

HRID 1816483 reaction equation
[Si]([O:8][C@H:9]1[CH2:34][CH2:33][C@@:32]2([CH3:35])[C@@H:11]([CH2:12][CH2:13][C:14]3[C:15]4[C@:28]([CH3:36])([CH2:29][CH2:30][C:31]=32)[C@@H:18]([C@H:19]([CH3:27])[CH2:20][CH2:21][C:22](=[O:26])[CH:23]([CH3:25])[CH3:24])[CH2:17][CH:16]=4)[C:10]1([CH3:38])[CH3:37])(C(C)(C)C)(C)C.Cl>C(O)C>[OH:8][C@H:9]1[CH2:34][CH2:33][C@@:32]2([CH3:35])[C@@H:11]([CH2:12][CH2:13][C:14]3[C:15]4[C@:28]([CH3:36])([CH2:29][CH2:30][C:31]=32)[C@@H:18]([C@H:19]([CH3:27])[CH2:20][CH2:21][C:22](=[O:26])[CH:23]([CH3:25])[CH3:24])[CH2:17][CH:16]=4)[C:10]1([CH3:38])[CH3:37]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 21349775HCID 21349775, compound

Product 1

HCID 9932250HCID 9932250, compoundYield 81.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3β-tert-Butyldimethylsilyloxy-4,4-dimethyl-5α-cholesta-8,14-dien-24-one (0.1 g) is dissolved in 5 ml of ethanol, 0.2 ml of 6N hydrogen chloride is added and the mixture is stirred for 2 days. After aqueous work-up, column chromatography and crystallization from ethanol/-water, the title compound (64 mg) is obtained. 1H-NMR (CDCl3, 400 MHz): δ=5.35 (1H, s); 8.24 (1H, m); 2.62 (1H, m). MS: Calculated: 426.7. Found 426.3.

Workup

  1. customAfter aqueous work-up, column chromatography and crystallization from ethanol/-water

Sources & evidence

ORD record
ord-9b67a74b5a7d4f5fb478ff1cd9e753a4
Source dataset
uspto-grants-2005_04
Patent number
US06884796B2

Reaction notes

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