Diethyl Ether → 3-Oxo-4,4-dimethyl-5alpha-chola-8,14-dien-24-aldehyde

HRID 479323Notes

Reaction equation

HRID 479323 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.C[N+]1([O-])CCOCC1.CCOCC>ClCCl.CCC[N+](CCC)(CCC)CCC.[O-][Ru](=O)(=O)=O>[O:25]=[C: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

6

Reactant 3

HCID 3283Diethyl EtherHCID 82029Methyl morpholine oxideHCID 155430924,4-Dimethyl-5alpha-chola-8,14-dien-3beta,24-diol

Product 1

HCID 155430933-Oxo-4,4-dimethyl-5alpha-chola-8,14-dien-24-aldehydeYield 70%

Reagents, catalysts & solvents 2

HCID 178419074HCID 178419074, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

A suspension of 4,4-dimethyl-5α-chola-8,14-dien-3β,24-diol (500 mg, 1.29 mmol), N-methylmorpholine-N-oxide (600 mg, 5.2 mmol), TPAP (45 mg, 0.13 mmol) and crushed molecular sieves (2 g) in dichloromethane (5 mL) was stirred for 30 minutes at room temperature. Addition of ether (15 mL) and filtration through kieselguhr gave a dark brown solution which was concentrated under reduced pressure and purified by chromatography (Eluant: 3 hexane: 1 ethyl acetate) to give the 3-oxo-4,4-dimethyl-5α-chola-8,14-dien-24-aldehyde (345 mg, 70%) as a white solid with melting point 96.5-97° C.

Workup

  1. customgave a dark brown solution which
  2. concentrationwas concentrated under reduced pressure
  3. custompurified by chromatography (Eluant: 3 hexane: 1 ethyl acetate)

Sources & evidence

ORD record
ord-b4e8c427fff54233bc72670401366d23
Source dataset
uspto-grants-2003_11
Patent number
US06645953B2

Reaction notes

Loading…