Cholesterol → (-)-beta-Sitosterol

HRID 903128Notes

Reaction equation

HRID 903128 reaction equation
[CH3:1][CH:2]([CH2:4][CH2:5][CH2:6][C@H:7]([C@@H:9]1[C@:27]2([CH3:28])[C@H:12]([C@H:13]3[C@H:24]([CH2:25][CH2:26]2)[C@:22]2([CH3:23])[C:16]([CH2:17][C@H:18]([CH2:20][CH2:21]2)[OH:19])=[CH:15][CH2:14]3)[CH2:11][CH2:10]1)[CH3:8])[CH3:3].[CH2:29]=[CH:30]CCCC.CC(CCC[C@H]([C@@H]1[C@]2(C)[C@H]([C@H]3[C@H](CC2)[C@]2(C)C(=CC(=O)CC2)CC3)CC1)C)C.C[C@@H]([C@@H]1[C@@]2(C)CC[C@@H]3[C@@]4(C)CCC(C[C@@H]4CC[C@H]3[C@@H]2CC1)=O)CCCC(C)C.CC(C(=O)CC[C@H]([C@@H]1[C@]2(C)[C@H]([C@H]3[C@H](CC2)[C@]2(C)C(CCCC2)CC3)CC1)C)C>C(C(C)=O)C>[CH3:29][CH2:30][C@@H:4]([CH:2]([CH3:1])[CH3:3])[CH2:5][CH2:6][C@H:7]([C@@H:9]1[C@@:27]2([CH3:28])[CH2:26][CH2:25][C@@H:24]3[C@@:22]4([CH3:23])[CH2:21][CH2:20][C@H:18]([OH:19])[CH2:17][C:16]4=[CH:15][CH2:14][C@H:13]3[C@@H:12]2[CH2:11][CH2:10]1)[CH3:8]

Participants

7

Reactant 5

HCID 5997Cholesterol2×HCID 115971-HexeneHCID 91477Cholest-4-en-3-oneHCID 921285alpha-Cholestan-3-oneHCID 54411711(6R)-6-[(8R,9S,10S,13R,14S,17R)-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]-2-methylheptan-3-one

Product 1

HCID 222284(-)-beta-Sitosterol

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

Cholesterol (20 g), methyl ethyl ketone (150 ml), and Girdler G65-S-RS catalyst (10.0 g) and 1-hexene (13 g) were heated and rocked at 250° C. for 4 hours. An analysis by gas chromatography indicated conversion to a mixture of 4-cholesten-3-one (78 parts), cholesterol (4 parts), coprostanone (8 parts), and cholestanone (6 parts). Similar results are obtained when sitosterol is used in place of cholesterol.

Workup

  1. customSimilar results

Sources & evidence

ORD record
ord-0c80bf1d890c4aab8563ff77cbe656be
Source dataset
uspto-grants-1980_10
Patent number
US04226786

Reaction notes

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