Bis(p-methoxyphenyl) telluroxide → (3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol acetate

HRID 1164690Notes

Reaction equation

HRID 1164690 reaction equation
[CH3:1][CH:2]([CH2:4][CH2:5][CH2:6][C@H:7]([C@@H:9]1[C@:26]2([CH3:27])[C@H:12]([C@H:13]3[C@H:23]([CH2:24][CH2:25]2)[C@:21]2([CH3:22])[C:16]([CH2:17][C@@H:18]([OH:28])[CH2:19][CH2:20]2)=[CH:15][CH2:14]3)[CH2:11][CH2:10]1)[CH3:8])[CH3:3].S=[CH:30][C:31]([O-:33])=[O:32].COC1C=CC([Te](C2C=CC(OC)=CC=2)=O)=CC=1>>[CH3:3][CH:2]([CH2:4][CH2:5][CH2:6][C@H:7]([C@@H:9]1[C@:26]2([CH3:27])[C@H:12]([C@H:13]3[C@H:23]([CH2:24][CH2:25]2)[C@:21]2([CH3:22])[C:16]([CH2:17][C@@H:18]([OH:28])[CH2:19][CH2:20]2)=[CH:15][CH2:14]3)[CH2:11][CH2:10]1)[CH3:8])[CH3:1].[C:31]([O-:33])(=[O:32])[CH3:30]

Participants

3

Reactant 2

HCID 3044917Bis(p-methoxyphenyl) telluroxideHCID 867387635-Cholesten-3beta-ol thionoacetate

Product 1

HCID 86738762(3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol acetateYield 100%

Procedure

5-Cholesten-3β-ol-thionoacetate (111 mg, 0.25 mmol), was reacted with bis-(p-methoxyphenyl)-telluroxide for 0.25 h. 5-Cholesten-3β-ol-acetate (107 mg, 100%) was obtained after P.l.c. (petroleum ether-ethyl acetate 9:1. The product obtained was recrystallized from acetone (90 mg, 84%), m.p. 113°-114° (lit., 114°-115°).

Sources & evidence

ORD record
ord-6d8aa0ddc6964191966a5adb4e7f156e
Source dataset
uspto-grants-1983_01
Patent number
US04370497

Reaction notes

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