Phosphorus pentachloride → 17,21-Diacetoxy-6-methylene-4-pregnene-3,20-dione

HRID 2059162Notes

Reaction equation

HRID 2059162 reaction equation
[C:1]([O:4][C@:5]1([C@:29]2([CH3:30])[C@H:15]([C@H:16]3[C@H:26]([CH2:27][CH2:28]2)[C@:24]2([CH3:25])[C:19](=[CH:20][C:21](=[O:31])[CH2:22][CH2:23]2)[CH2:18][CH2:17]3)[CH2:14][CH2:13]1)[C:6](=[O:12])[CH2:7][O:8][C:9](=[O:11])[CH3:10])(=[O:3])[CH3:2].[C:32]([O-])(=O)C.[Na+].P(Cl)(Cl)(Cl)(Cl)Cl>C(Cl)Cl.COCOC>[C:1]([O:4][C@:5]1([C@:29]2([CH3:30])[C@H:15]([C@H:16]3[C@H:26]([CH2:27][CH2:28]2)[C@:24]2([CH3:25])[C:19](=[CH:20][C:21](=[O:31])[CH2:22][CH2:23]2)[C:18](=[CH2:32])[CH2:17]3)[CH2:14][CH2:13]1)[C:6](=[O:12])[CH2:7][O:8][C:9](=[O:11])[CH3:10])(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 24819Phosphorus pentachlorideHCID 10216517,21-Bis(acetyloxy)pregn-4-ene-3,20-dioneHCID 517045Sodium Acetate

Product 1

HCID 1295177117,21-Diacetoxy-6-methylene-4-pregnene-3,20-dioneYield 58.9%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8020DimethoxymethaneSolvent

Procedure

A solution of 2.0 g of 17,21-diacetoxy-4-pregnene-3,20-dione in 60 ml of methylene chloride and 60 ml of formaldehyde dimethylacetal is refluxed for 30 hours with 2.0 g of sodium acetate and 12.6 g of phosphorus pentachloride. The mixture is worked up analogously to Example 9, thus isolating 1.21 g of 17,21-diacetoxy-6-methylene-4-pregnene-3,20-dione, mp 227°-228° C.

Sources & evidence

ORD record
ord-61426a9f0186448ba939e3e6c6b2426c
Source dataset
uspto-grants-1982_03
Patent number
US04322349

Reaction notes

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