Dimethoxymethane → HCID 53683694, compound

HRID 2059160Notes

Reaction equation

HRID 2059160 reaction equation
[C:1]([O:4][CH2:5][C@@:6]12[C@@H:25]3[C@H:14]([C@H:15]4[C@:22]([CH3:26])([CH2:23][CH2:24]3)[C@@:18]([O:27][C:28](=[O:34])[CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])([C:19](=[O:21])[CH3:20])[CH2:17][CH2:16]4)[CH2:13][CH2:12][C:11]1=[CH:10][C:9](=[O:35])[CH2:8][CH2:7]2)(=[O:3])[CH3:2].[CH3:36]OCOC.O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O>C(Cl)Cl>[C:1]([O:4][CH2:5][C@@:6]12[C@@H:25]3[C@H:14]([C@H:15]4[C@:22]([CH3:26])([CH2:23][CH2:24]3)[C@@:18]([O:27][C:28](=[O:34])[CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])([C:19](=[O:21])[CH3:20])[CH2:17][CH2:16]4)[CH2:13][C:12](=[CH2:36])[C:11]1=[CH:10][C:9](=[O:35])[CH2:8][CH2:7]2)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 8020DimethoxymethaneHCID 14812Phosphorus oxide (P4O10)HCID 56621802HCID 56621802, compound

Product 1

HCID 53683694HCID 53683694, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Analogously to Example 1, 1.0 g of 19-acetoxy-17-hexanoyloxy-4-pregnene-3,20-dione in 7 ml of methylene chloride is reacted with 4.9 ml of formaldehyde dimethylacetal and a mixture of 200 mg of phosphorus pentoxide and 1.5 g of kieselguhr W 20, and worked up. The crude product is purified on 110 g of silica gel with a hexane/acetone gradient (0-20% acetone), thus isolating 563 mg of 19-acetoxy-17-hexanoyloxy-6-methylene-4-pregnene-3,20-dione, mp 111°-112° C.

Workup

  1. customThe crude product is purified on 110 g of silica gel with a hexane/acetone gradient (0-20% acetone)

Sources & evidence

ORD record
ord-5e1c8d68687d4154af55e38e883d8109
Source dataset
uspto-grants-1982_03
Patent number
US04322349

Reaction notes

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