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

HRID 2059161Notes

Reaction equation

HRID 2059161 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].[CH3:32]OCOC.C([O-])(=O)C.[Na+].P(Br)(Br)(Br)=O>C(Cl)Cl>[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 4

HCID 8020DimethoxymethaneHCID 24613Phosphorus oxybromideHCID 10216517,21-Bis(acetyloxy)pregn-4-ene-3,20-dioneHCID 517045Sodium Acetate

Product 1

HCID 1295177117,21-Diacetoxy-6-methylene-4-pregnene-3,20-dione

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Analogously to Example 9, 2.0 g of 17,21-diacetoxy-4-pregnene-3,20-dione in 60 ml of methylene chloride is reacted with 60 ml of formaldehyde dimethylacetal, 2.0 g of sodium acetate, and 12.6 g of phosphorus oxybromide, and worked up, thus isolating 1.68 g of 17,21-diacetoxy-6-methylene-4-pregnene-3,20-dione, mp 226°-228° C.

Sources & evidence

ORD record
ord-7bd1b1443d4f4ef6a1c312bb8a82d656
Source dataset
uspto-grants-1982_03
Patent number
US04322349

Reaction notes

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