huagongshe.com
HRID274309

反应详情

EQUATION

反应方程式

HRID 274309 的结构方程式

REACTANTS

反应物

3
结构：C=O
HCID712

Formaldehyde

CH2O

结构：C[NH2+]c1ccccc1.O=C([O-])C(F)(F)F
HCID2724109

N-Methylanilinium trifluoroacetate

C9H10F3NO2

结构：C[C@]12CCC(=O)C=C1CC[C@@H]1[C@@H]2CC[C@@]2(C)[C@H]1C=C[C@]2(C)O
HCID15679136

未命名化合物

PRODUCTS

生成物

1
结构：C=C1C[C@@H]2[C@H](CC[C@@]3(C)[C@H]2C=C[C@]3(C)O)[C@@]2(C)CCC(=O)C=C12
HCID15679149

未命名化合物

收率 43.5%

AUXILIARIES

试剂、催化剂与溶剂

2
结构：C1CCOC1
溶剂HCID8028

Tetrahydrofuran

C4H8O

结构：CCOC(C)=O
溶剂HCID8857

Ethyl acetate

C4H8O2

PROCEDURE

实验过程

500 mg of 17β-hydroxy-17α-methylandrosta-4,15-dien-3-one in 8.3 ml of tetrahydrofuran is stirred at 60° C. under argon with 348 mg of paraformaldehyde and 2.2 g of N-methylanilinium trifluoroacetate. After 3.5 hours, the mixture is diluted with ethyl acetate, washed with water, dried over sodium sulfate, and concentrated under vacuum. After the crude product has been chromatographed on silica gel with a pentane-diethyl ether gradient, 226 mg of 17β-hydroxy-17α-methyl-6-methyleneandrosta-4,15-dien-3-one is obtained, mp 162° C. (from isopropyl ether).

WORKUP

后处理

  1. washwashed with water
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated under vacuum
  4. customAfter the crude product has been chromatographed on silica gel with a pentane-diethyl ether gradient