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

HRID 971434

Reaktionsgleichung

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]

Komponenten

Edukt 4

HCID 7865Methyl formate

HCID 24758Sodium hydride

HCID 2365364-Methyltestosterone

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

Produkt 1

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

Versuchsvorschrift

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.

Aufarbeitung

customof product obtained
customwas used directly in the next reaction

Quellen und Nachweise

ORD-Eintrag: ord-8c4c7750dc934c27b5fb5795da79a057
Quelldatensatz: uspto-grants-1979_07
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US04160027

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