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

HRID 1764958Notes

Reaction equation

HRID 1764958 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.[Ru](Cl)Cl.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=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

4

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 2

HCID 11007548Dichlorotris(triphenylphosphine)rutheniumCatalystHCID 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-ba03ed908c4c40fba6e896d872cc9e14
Source dataset
uspto-grants-2007_06
Patent number
USRE039678E1

Reaction notes

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