Oxygen → 25-Hydroxy-7-dehydrocholesterol

HRID 839279Notes

Reaction equation

[CH3:1][C:2]([OH:29])([CH2:4][CH2:5][CH2:6][C@H:7]([C@@H:9]1[C@:26]2([CH3:27])[C@H:12]([C: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][CH:14]=3)[CH2:11][CH2:10]1)[CH3:8])[CH3:3].O=O>>[CH3:1][C:2]([OH:29])([CH2:4][CH2:5][CH2:6][C@H:7]([C@@H:9]1[C@:26]2([CH3:27])[C@H:12]([C: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][CH:14]=3)[CH2:11][CH2:10]1)[CH3:8])[CH3:3]

Participants

Reactant 2

HCID 977Oxygen

HCID 2279535225-Hydroxylumisterol

Product 1

HCID 990898325-Hydroxy-7-dehydrocholesterol

Procedure

9β,10α-cholesta-5,7-diene-3β,25-diol (5.0 g.) in 1 l. dry oxygen-free tetrahydrofuran, is irradiated in a like fashion to that described in Example 1. Working up in an analogous fashion to Example 1, some cholesta-5,7-diene-3β,25-diol is initially isolated. After a thermal treatment of the materials contained in the filtrate, similar to that of Example 1, 25-hydroxycholecalciferol is isolated.

Sources & evidence

ORD record: ord-39b9c6a0c2d4499c921eac83a9bf4f3d
Source dataset: uspto-grants-1978_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04094890

Reaction notes

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