Ammonium Chloride → 3-Fluoromethylene-19-methylthio-4-androsten-17-one

HRID 1650786ノート

反応式

HRID 1650786 の反応式
[CH3:1][S:2][CH2:3][C@@:4]12[C@@H:21]3[C@H:12]([C@H:13]4[C@@:17]([CH2:19][CH2:20]3)([CH3:18])[C:16](=[O:22])[CH2:15][CH2:14]4)[CH2:11][CH2:10][C:9]1=[CH:8][C:7](=O)[CH2:6][CH2:5]2.F[B-](F)(F)F.[F:29][CH2:30][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C([Li])CCC.[Cl-].[NH4+]>C(COC)OC.O>[F:29][CH:30]=[C:7]1[CH2:6][CH2:5][C@@:4]2([CH2:3][S:2][CH3:1])[C:9]([CH2:10][CH2:11][C@@H:12]3[C@@H:21]2[CH2:20][CH2:19][C@@:17]2([CH3:18])[C@H:13]3[CH2:14][CH2:15][C:16]2=[O:22])=[CH:8]1

参加物

7

反応物 4

HCID 25517Ammonium ChlorideHCID 14614219-Thiomethylandrost-4-ene-3,17-dioneHCID 11303586(Fluoromethyl)triphenylphosphonium tetrafluoroborateHCID 178418339Butyllithium

生成物 1

HCID 536819483-Fluoromethylene-19-methylthio-4-androsten-17-one

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 80711,2-Dimethoxyethane溶媒2 回

実験手順

500 ml of 19-methylthio-4-androsten-3,17-dione (Euoprean patent 100,566) in 10 ml of dimethoxyethane is added drop by drop at 0° C. to a suspension of 5.73 g of fluoromethyl triphenylphosphonium tetrafluoroborate in 40 ml of dimethoxyethane, which was stirred with 9.5 ml of butyllithium solution (1.6 m in ether) for 0.5 hour, instilled and stirred for another 15 minutes. Then saturated ammonium chloride solution is added, diluted with water, extracted three times with ethyl acetate, washed neutral, dried on sodium sulfate and concentrated in a vacuum. After chromatography on silica gel with hexane/ethyl acetate, 331 mg of pure 3-fluoromethylene-19-methylthio-4-androsten-17-one with a melting point of 146°-147° C. [α]D +288.4° (CHCl3) as E:Z mixture is obtained.

後処理

  1. extractionextracted three times with ethyl acetate
  2. washwashed neutral
  3. customdried on sodium sulfate
  4. concentrationconcentrated in a vacuum

出典と根拠

ORDレコード
ord-88bbf6e46244461ba746550bf69e2cea
出典データセット
uspto-grants-1990_05
特許番号
US04925834

反応ノート

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