Methyl formate → 17beta-Hydroxy-2-hydroxymethylene-6alpha-methylandrost-4-en-3-one

HRID 971435Notes

Reaction equation

HRID 971435 reaction equation
[OH:1][C@H:2]1[CH2:7][CH2:6][C@H:5]2[C@H:8]3[C@H:18]([CH2:19][CH2:20][C@:3]12[CH3:4])[C@:16]1([CH3:17])[C:11](=[CH:12][C:13](=[O:21])[CH2:14][CH2:15]1)[C@@H:10]([CH3:22])[CH2:9]3.[CH:23](OC)=[O:24].C[O-].[Na+].O[C@@]1(C)CC[C@H]2[C@H]3[C@H](CC[C@]12C)[C@]1(C)C(=C(C)C(=O)C(=CO)C1)CC3>O1CCCC1.CO>[OH:1][C@H:2]1[CH2:7][CH2:6][C@H:5]2[C@H:8]3[C@H:18]([CH2:19][CH2:20][C@:3]12[CH3:4])[C@:16]1([CH3:17])[C:11](=[CH:12][C:13](=[O:21])[C:14](=[CH:23][OH:24])[CH2:15]1)[C@@H:10]([CH3:22])[CH2:9]3

Participants

7

Reactant 4

HCID 7865Methyl formateHCID 2364176alpha-MethyltestosteroneHCID 10942334Sodium MethoxideHCID 573496094,17alpha-Dimethyl-2-hydroxymethylene Testosterone

Product 1

HCID 7060332617beta-Hydroxy-2-hydroxymethylene-6alpha-methylandrost-4-en-3-one

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

17β-Hydroxy-2-hydroxymethylene-6α-methylandrost-4-en-3-one was prepared from 286 g. of 17β-hydroxy-6α-methylandrost-4-en-3-one (6α-methyltestosterone), 410 ml. of methyl formate, 140 g. of sodium methoxide, 40 ml. of methanol and 3 l. of tetrahydrofuran according to the procedure of Example 1, part (c). The total product, obtained nearly quantitative yield as an amber glass was used directly in the next reaction.

Workup

  1. customThe total product, obtained nearly quantitative yield as an amber glass
  2. customwas used directly in the next reaction

Sources & evidence

ORD record
ord-8999705e8090481b8976251e836de4c8
Source dataset
uspto-grants-1979_07
Patent number
US04160027

Reaction notes

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