Bis(p-methoxyphenyl) telluroxide → 5-Cholesten-3beta-thiol benzoate

HRID 1164691Notes

Reaction equation

HRID 1164691 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](O)[CH2:19][CH2:20]2)=[CH:15][CH2:14]3)[CH2:11][CH2:10]1)[CH3:8])[CH3:3].[S:29]=[C:30]1[CH:38]=[CH:37][CH:36]=[C:32]([C:33]([O-:35])=[O:34])[C:31]1=S.COC1C=CC([Te](C2C=CC(OC)=CC=2)=O)=CC=1>>[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]([SH:29])[CH2:19][CH2:20]2)=[CH:15][CH2:14]3)[CH2:11][CH2:10]1)[CH3:8])[CH3:3].[C:33]([O-:35])(=[O:34])[C:32]1[CH:36]=[CH:37][CH:38]=[CH:30][CH:31]=1

Participants

3

Reactant 2

HCID 3044917Bis(p-methoxyphenyl) telluroxideHCID 867387655-Cholesten-3beta-ol dithionobenzoate

Product 1

HCID 867387645-Cholesten-3beta-thiol benzoateYield 70%

Procedure

5-Cholesten-3β-ol-dithionobenzoate (130 mg, 0.25 mmol) was reacted with bis-(p-methoxyphenyl)-telluroxide for 27 h. 5-Cholesten-3β-thiol-benzoate (88 mg, 70%), m.p. 160°-162° was obtained after p.l.c. (petroleum ether-ethyl acetate 20:1). The product obtained was recrystallised from ethyl acetate (65 mg, 52%), m.p. 164.5-166 (lit., 167°), νmax. (CCl4) 2800,2750,1670,1550,1250,1210,1180,920,865,810-740 (broad) and 700 cm-1, m/e 506 (M+ weak), 369, and 368 (100%).

Sources & evidence

ORD record
ord-04461a92b16145cea849676f32f8f4de
Source dataset
uspto-grants-1983_01
Patent number
US04370497

Reaction notes

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