2-Iodoxybenzoic acid → 5alpha-Cholestan-3-one
Reaction equation
[CH3:1][C@@H:2]([C@@H:9]1[C@@:13]2([CH3:28])[CH2:14][CH2:15][CH2:16]/[C:17](=[CH:18]\[CH:19]=[C:20]3\[CH2:21][C@@H:22]([OH:27])[CH2:23][CH2:24][C:25]\3=[CH2:26])/[C@@H:12]2[CH2:11][CH2:10]1)[CH2:3][CH2:4][CH2:5][CH:6]([CH3:8])[CH3:7].I(C1C=CC=CC=1C(O)=O)(=O)=O>C1COCC1.CS(C)=O>[CH3:8][CH:6]([CH2:5][CH2:4][CH2:3][C@H:2]([C@@H:9]1[C@:13]2([CH3:28])[C@H:12]([C@H:17]3[C@H:16]([CH2:15][CH2:14]2)[C@:25]2([CH3:26])[C@H:20]([CH2:21][C:22](=[O:27])[CH2:23][CH2:24]2)[CH2:19][CH2:18]3)[CH2:11][CH2:10]1)[CH3:1])[CH3:7]Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Procedure
A solution of dihydrocholesterol (1.94 g; 5 mmol) in THF (8 ml) was added to a solution of o-iodoxybenzoic acid I (2.10 g, 7.5 mmol) in DMSO (14 ml). After 2 hr precipitation of a white solid was observed. After 5 hr the reaction solution was poured into Na2CO3 (5%, 40 ml) and extracted with diethyl ether/n-hexane (50:50; 3×30 ml). The combined organic layers were washed with water (2×15 ml), dried over sodium sulfate and brought to dryness under vacuum. The residue was crystallised from ethanol to give 1.73 g (89%) of 5α-cholestan-3-one mp 129°-130° C. (lit. 128°-130° C.: Beilsteins Handbuch der organischen Chemie, III E., 7, 1330b).
Workup
- customAfter 2 hr precipitation of a white solid
- additionAfter 5 hr the reaction solution was poured into Na2CO3 (5%, 40 ml)
- extractionextracted with diethyl ether/n-hexane (50:50; 3×30 ml)
- washThe combined organic layers were washed with water (2×15 ml)
- dry with materialdried over sodium sulfate
- customThe residue was crystallised from ethanol
Sources & evidence
- ORD record
- ord-06d285a44fc04e99a54b88fb3cc8b653
- Source dataset
- uspto-grants-1996_04
- Patent number
- US05510538
Reaction notes
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