Methyl formate → 2-Hydroxymethylene-17beta-hydroxy-4-methylandrost-4-en-3-one

HRID 971434

Reaction equation

O[C@H]1CC[C@H]2[C@H]3[C@H](CC[C@]12C)[C@]1(C)C(=C(C)C(=O)CC1)CC3.C(OC)=O.[OH:27][C@@:28]1(C)[CH2:33][CH2:32][C@H:31]2[C@H:34]3[C@H:44]([CH2:45][CH2:46][C@:29]12[CH3:30])[C@:42]1([CH3:43])[C:37](=[C:38]([CH3:50])[C:39](=[O:49])[C:40](=[CH:47][OH:48])[CH2:41]1)[CH2:36][CH2:35]3.[H-].[Na+]>>[OH:48][CH:47]=[C:40]1[CH2:41][C@@:42]2([CH3:43])[C:37]([CH2:36][CH2:35][C@@H:34]3[C@@H:44]2[CH2:45][CH2:46][C@@:29]2([CH3:30])[C@H:31]3[CH2:32][CH2:33][C@@H:28]2[OH:27])=[C:38]([CH3:50])[C:39]1=[O:49]

Participants

Reactant 4

HCID 7865Methyl formate

HCID 24758Sodium hydride

HCID 2365364-Methyltestosterone

HCID 573496094,17alpha-Dimethyl-2-hydroxymethylene Testosterone

Product 1

HCID 706032882-Hydroxymethylene-17beta-hydroxy-4-methylandrost-4-en-3-one

Procedure

2-Hydroxymethylene-17β-hydroxy-4-methylandrost-4-en-3-one was prepared from 32.28 g. of 17β-hydroxy-4-methylandrost-4-en-3-one and 32 ml. of methyl formate by a procedure analogous to that of Example 1, part (c) except that sodium hydride (15 g., 50%) was used in place of sodium methoxide. The 20 g. of product obtained was used directly in the next reaction.

Workup

customof product obtained
customwas used directly in the next reaction

Sources & evidence

ORD record: ord-8c4c7750dc934c27b5fb5795da79a057
Source dataset: uspto-grants-1979_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04160027

Linked notes

Loading…