Diethoxymethane → HCID 86737031, compound

HRID 1706404Notes

Reaction equation

HRID 1706404 reaction equation
[C:1]([O:4][CH2:5][C:6](=[O:31])[C@:7]1([OH:30])[C@:24]2([CH3:25])[C@H:10]([C@H:11]3[C@H:21]([C@@H:22]([O:26][CH:27]=[O:28])[CH2:23]2)[C@:19]2([CH3:20])[C:14](=[CH:15][C:16](=[O:29])[CH:17]=[CH:18]2)[CH2:13][CH2:12]3)[CH2:9][CH2:8]1)(=[O:3])[CH3:2].[CH2:32]([O:34][CH2:35]OCC)[CH3:33].O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O>C(Cl)Cl>[C:1]([O:4][CH2:5][C:6](=[O:31])[C@:7]1([O:30][CH2:35][O:34][CH2:32][CH3:33])[C@:24]2([CH3:25])[C@H:10]([C@H:11]3[C@H:21]([C@@H:22]([O:26][CH:27]=[O:28])[CH2:23]2)[C@:19]2([CH3:20])[C:14](=[CH:15][C:16](=[O:29])[CH:17]=[CH:18]2)[CH2:13][CH2:12]3)[CH2:9][CH2:8]1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 10024DiethoxymethaneHCID 14812Phosphorus oxide (P4O10)HCID 22811287HCID 22811287, compound

Product 1

HCID 86737031HCID 86737031, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5.0 g. of 21-acetoxy-11β-formyloxy-17α-hydroxy-1,4-pregnadiene-3,20-dione is dissolved in 150 ml. of methylene chloride and 30 ml. of formaldehyde diethylacetal and cooled to 0° C. Under agitation, a mixture of 5 g. of phosphorus pentoxide and 10 g. of kieselguhr is inroduced, and the mixture is stirred for 2.5 hours in an ice bath, whereafter it is filtered, washed with methylene chloride, and brought to pH 9 with triethylamine. After the solvent has been distilled off, 10.5 g. of crude 21-acetoxy-17α-ethoxymethoxy-11β-formyloxy-1,4-pregnadiene-3,20-dione is obtained as a semisolid mass.

Workup

  1. additionUnder agitation, a mixture of 5 g
  2. filtrationis filtered
  3. washwashed with methylene chloride
  4. distillationAfter the solvent has been distilled off

Sources & evidence

ORD record
ord-51694d28f03c4573ab40dcced8f5bba3
Source dataset
uspto-grants-1980_06
Patent number
US04207316

Reaction notes

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