Diethoxymethane → HCID 66852514, compound

HRID 1193466Notes

Reaction equation

HRID 1193466 reaction equation
[C:1]([O-])(=O)C.[Na+].C(OCOCC)C.P(Cl)(Cl)(Cl)=O.[CH2:18]1[C@@H:20]2[C:21](=[O:39])[CH:22]=[C:23]3[C@:36]([CH3:37])([CH:19]12)[C@@H:35]1[C@H:26]([C@H:27]2[C@@:31]([CH2:33][CH2:34]1)([CH3:32])[C:30](=[O:38])[CH2:29][CH2:28]2)[CH2:25][CH2:24]3.C(=O)([O-])[O-].[Na+].[Na+]>C(Cl)(Cl)Cl>[CH2:18]1[C@@H:20]2[C:21](=[O:39])[CH:22]=[C:23]3[C@:36]([CH3:37])([CH:19]12)[C@@H:35]1[C@H:26]([C@H:27]2[C@@:31]([CH2:33][CH2:34]1)([CH3:32])[C:30](=[O:38])[CH2:29][CH2:28]2)[CH2:25][C:24]3=[CH2:1]

Participants

7

Reactant 5

HCID 10024DiethoxymethaneHCID 10340Sodium CarbonateHCID 24813Phosphorus oxychlorideHCID 517045Sodium AcetateHCID 13564888HCID 13564888, compound

Product 1

HCID 66852514HCID 66852514, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A mixture of sodium acetate (1 g), absolute chloroform (30 ml), formaldehyde diethyl acetal (30 ml, 0.24 mol), phosphoryl chloride (3.8 ml, 40 mmol), and 1,2β-methylenandrost-4-ene-3,17-dione (0.806 g, 2.7 mmol) is stirred at reflux for about 7 hours, i.e. until the starting material has disappeared. The suspension is allowed to cool and under vigorous stirring a saturated sodium carbonate solution is added dropwise until the pH of the aqueous layer becomes alkaline (about 1 hour). The organic layer is separated, neutralized with water, and dried with sodium sulfate. After concentration under reduced pressure the oily residue is purified by column chromatography on silica gel using n-hexane/ethylacetate as eluant. The pure title compound is obtained in 60% yield (0.503 g).

Workup

  1. temperatureat reflux for about 7 hours
  2. temperatureto cool
  3. additionis added dropwise until the pH of the aqueous layer
  4. custom(about 1 hour)
  5. customThe organic layer is separated
  6. dry with materialdried with sodium sulfate
  7. concentrationAfter concentration under reduced pressure the oily residue
  8. customis purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-5f0b5d173ef143f3b3d2817d26c4b36f
Source dataset
uspto-grants-1989_03
Patent number
US04810423

Reaction notes

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