Hydrochloric Acid → HCID 67780909, compound

HRID 274314Notes

Reaction equation

HRID 274314 reaction equation
[CH3:1][O-:2].[Na+].[OH:4][C@@:5]1([CH3:26])[CH2:10][CH2:9][C@H:8]2[C@H:11]3[C@H:21]([CH2:22][CH2:23][C@:6]12[CH3:7])[C@:19]1([CH3:20])[C:14](=[CH:15][C:16](=[O:24])[CH2:17][CH2:18]1)[C:13](=[CH2:25])[CH2:12]3.Cl>N1C=CC=CC=1.COC=O.C(OCC)(=O)C>[OH:4][C@@:5]1([CH3:26])[CH2:10][CH2:9][C@H:8]2[C@H:11]3[C@H:21]([CH2:22][CH2:23][C@:6]12[CH3:7])[C@:19]1([CH3:20])[C:14](=[CH:15][C:16](=[O:24])/[C:17](=[CH:1]\[OH:2])/[CH2:18]1)[C:13](=[CH2:25])[CH2:12]3

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 10942334Sodium MethoxideHCID 12951792HCID 12951792, compound

Product 1

HCID 67780909HCID 67780909, compoundYield 64.3%

Reagents, catalysts & solvents 3

HCID 1049PyridineSolventHCID 7865Methyl formateSolventHCID 8857Ethyl AcetateSolvent

Procedure

At room temperature, 2.2 g of sodium methylate is added to 3.0 g of 17β-hydroxy-17α-methyl-6-methyleneandrost-4-en-3-one (Tetrahedron 20: 597, 1964) in 70 ml of pyridine and 10.2 ml of formic acid methyl ester. After 18 hours, the reaction mixture is stirred into ice/water which contains hydrochloric acid. The precipitated product is suctioned off, dissolved in ethyl acetate, washed with water, and dried over sodium sulfate. Chromatography of the crude product on silica gel with a methylene chloride-(tert-butyl methyl ether) gradient yields 2.1 g of (Z)-17β-hydroxy-2-hydroxymethylene-17α-methyl-6-methyleneandrost-4-en-3-one as a foam.

Workup

  1. washwashed with water
  2. dry with materialdried over sodium sulfate

Sources & evidence

ORD record
ord-db2eae75fe6d4a338911a1f9d249cb99
Source dataset
uspto-grants-1995_02
Patent number
US05389624

Reaction notes

Loading…