Benzene → 4-Methoxy-6-methylenandrost-4-ene-3,17-dione

HRID 620679ノート

反応式

HRID 620679 の反応式
[OH:1][C:2]1[C:19](=[O:20])[CH2:18][CH2:17][C@@:16]2([CH3:21])[C:3]=1[C:4](=[CH2:23])[CH2:5][C@@H:6]1[C@@H:15]2[CH2:14][CH2:13][C@@:11]2([CH3:12])[C@H:7]1[CH2:8][CH2:9][C:10]2=[O:22].[CH:24]1C=CC=CC=1.IC>>[CH3:24][O:1][C:2]1[C:19](=[O:20])[CH2:18][CH2:17][C@@:16]2([CH3:21])[C:3]=1[C:4](=[CH2:23])[CH2:5][C@@H:6]1[C@@H:15]2[CH2:14][CH2:13][C@@:11]2([CH3:12])[C@H:7]1[CH2:8][CH2:9][C:10]2=[O:22]

参加物

4

反応物 3

HCID 241BenzeneHCID 6328Methyl iodideHCID 186318864-Hydroxy-6-methylenandrost-4-ene-3,17-dione

生成物 1

HCID 186318914-Methoxy-6-methylenandrost-4-ene-3,17-dione収率 75.2%

実験手順

To a solution of 4-hydroxy-6-methylenandrost-4-ene-3,17-dione (0.315 g, 1 mmole) in benzene (10 ml) potassium tert-butoxide (0.224 g, 2 mmole) is added and the mixture heated to reflux for 30 minutes. After cooling, iodomethane (0.710 g, 5 mmole) is added and the mixture boiled for a further 2 hours. Then the organic solution is washed with water, dried and evaporated in vacuum. Flash column chromatography of the residue on silica gel using n-hexane/ethyl acetate 60:40 affords 0.247 g (75% yield) of the title compound, m.p. 196°-198° C.

後処理

  1. temperaturethe mixture heated
  2. temperatureto reflux for 30 minutes
  3. temperatureAfter cooling
  4. washThen the organic solution is washed with water
  5. customdried
  6. customevaporated in vacuum

出典と根拠

ORDレコード
ord-2a4c1910f78941c1b51724d1e4461bca
出典データセット
uspto-grants-1989_04
特許番号
US04822528

反応ノート

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