4,4-Dimethyl-5alpha-chola-8,14-dien-3beta,24-diol → 3beta-Hydroxy-4,4-dimethyl-5alpha-chola-8,14-dien-24-aldehyde

HRID 2187276Notes

Reaction equation

HRID 2187276 reaction equation
[CH3:1][C:2]1([CH3:28])[C@@H:24]([OH:25])[CH2:23][CH2:22][C@@:21]2([CH3:26])[C@H:3]1[CH2:4][CH2:5][C:6]1[C:7]3[C@:17]([CH3:27])([CH2:18][CH2:19][C:20]=12)[C@@H:10]([C@H:11]([CH3:16])[CH2:12][CH2:13][CH2:14][OH:15])[CH2:9][CH:8]=3>C1C=CC=CC=1>[OH:25][C@H:24]1[CH2:23][CH2:22][C@@:21]2([CH3:26])[C@@H:3]([CH2:4][CH2:5][C:6]3[C:7]4[C@:17]([CH3:27])([CH2:18][CH2:19][C:20]=32)[C@@H:10]([C@H:11]([CH3:16])[CH2:12][CH2:13][CH:14]=[O:15])[CH2:9][CH:8]=4)[C:2]1([CH3:1])[CH3:28]

Participants

3

Reactant 1

HCID 155430924,4-Dimethyl-5alpha-chola-8,14-dien-3beta,24-diol

Product 1

HCID 155430943beta-Hydroxy-4,4-dimethyl-5alpha-chola-8,14-dien-24-aldehydeYield 61.8%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

4,4-Dimethyl-5α-chola-8,14-dien-3β,24-diol (0.21 g) is dissolved in benzene (21 ml). Tris(triphenylphosphine)ruthenium(II)chloride (1.04 g) is added and the mixture is stirred at room temperature for 20 hours. Purification by column chromatography gives the title compound (129 mg). 1H-NMR (CDCl3, 300 MHz): δ=9.79 (1H, s); 5.36 (1H, s); 1.05 (3H, s), 1.01 (3H, s); 0.95 (3H, d); 0.82 (3H, s); 0.80 (3H, s).

Workup

  1. customPurification by column chromatography

Sources & evidence

ORD record
ord-44a1e5626a244bb58600adf1f7eb82b8
Source dataset
uspto-grants-2002_06
Patent number
US06407086B2

Reaction notes

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