Methanol, 1-methoxy-, 1-acetate → 17alpha,21-Diacetoxy-6-methyl-4,6-pregnadiene-3,20-dione

HRID 325280Notes

Reaction equation

[C:1]([O-])(=O)C.[Na+].C(OCOC)(=O)C.[C:13]([O:16][C@:17]1([C@:41]2([CH3:42])[C@H:27]([C@H:28]3[C@H:38]([CH2:39][CH2:40]2)[C@:36]2([CH3:37])[C:31](=[CH:32][C:33](=[O:43])[CH2:34][CH2:35]2)[CH2:30][CH2:29]3)[CH2:26][CH2:25]1)[C:18](=[O:24])[CH2:19][O:20][C:21](=[O:23])[CH3:22])(=[O:15])[CH3:14]>C(Cl)(Cl)Cl.P(Cl)(Cl)(Cl)=O>[C:13]([O:16][C@:17]1([C@:41]2([CH3:42])[C@H:27]([C@H:28]3[C@H:38]([CH2:39][CH2:40]2)[C@:36]2([CH3:37])[C:31](=[CH:32][C:33](=[O:43])[CH2:34][CH2:35]2)[C:30]([CH3:1])=[CH:29]3)[CH2:26][CH2:25]1)[C:18](=[O:24])[CH2:19][O:20][C:21](=[O:23])[CH3:22])(=[O:15])[CH3:14]

Participants

Conditions

Temperature: 60 °C

Procedure

Under argon, a suspension of 0.5 g of sodium acetate in 60 ml of anhydrous chloroform, 2 ml of distilled phosphorus oxychloride, and 15 ml of methoxymethyl acetate is agitated for 30 minutes at a bath temperature of 60° C. After adding 2.0 g of 17α,21-diacetoxy-4-pregnene-3,20-dione, the mixture is further stirred for 3 hours at 70° C. and worked up analogously to Example 1. The dark crude product is purified on 200 g of silica gel with a hexane-ethyl acetate gradient (0-40% ethyl acetate), yielding 1.15 g of 17α,21-diacetoxy-6-methyl-4,6-pregnadiene-3,20-dione, mp 213°-215° C.

Workup

stirringthe mixture is further stirred for 3 hours at 70° C.
customThe dark crude product is purified on 200 g of silica gel with a hexane-ethyl acetate gradient (0-40% ethyl acetate)

Sources & evidence

ORD record: ord-fc3ea11338344e7e9ca20a6f4c6e62ec
Source dataset: uspto-grants-1984_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04440684

Reaction notes

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