Water → 9-Dehydroandrostenedione

HRID 1087672

反応式

HRID 1087672 の反応式
O[C@:2]12[CH2:19][CH2:18][C@@:16]3([CH3:17])[C@@H:12]([CH2:13][CH2:14][C:15]3=[O:20])[C@@H:11]1[CH2:10][CH2:9][C:8]1[C@:3]2([CH3:22])[CH2:4][CH2:5][C:6](=[O:21])[CH:7]=1.ClS(O)(=O)=O.O.CCCCCCC>C(Cl)Cl>[CH3:17][C@:16]12[CH2:18][CH:19]=[C:2]3[C@@H:11]([CH2:10][CH2:9][C:8]4[C@:3]3([CH3:22])[CH2:4][CH2:5][C:6](=[O:21])[CH:7]=4)[C@@H:12]1[CH2:13][CH2:14][C:15]2=[O:20]

参加物

6

反応物 4

HCID 962WaterHCID 8900HeptaneHCID 24638Chlorosulfonic acidHCID 104250179alpha-Hydroxyandrost-4-ene-3,17-dione

生成物 1

HCID 2395959-Dehydroandrostenedione

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

9α-Hydroxyandrostenedione (5.00 g.) is dissolved in methylene chloride (50 ml.) and cooled to 0°-5°. A solution of chlorosulfonic acid (2.5 ml.) in methylene chloride (10 ml.) is added slowly over a period of 4 minutes. At the end of the addition TLC shows the reaction is completed. Water (60 ml.) is added to the reaction mixture keeping the temperature at 3°-15°. The mixture is stirred for 2 minutes and heptane (135 ml.) is added. The organic phase is separated and washed twice with water (30 ml. each time). The organic phase is concentrated with heat to about 30 ml. with crystals forming as the solution cools. The mixture is cooled to 0°-5°, filtered, washed with a minimum amount of heptane, and dried at 70° to give androsta-4,9(11)-diene-3,17-dione; 4.45 g. (89.0% weight yield, 94.7% chemical yield), m.p., 195.5°-202°; [α]D +220° (chloroform); UV (methanol) λmax =240 nm (ε=16,300).

後処理

  1. temperaturecooled to 0°-5°
  2. customat 3°-15°
  3. customThe organic phase is separated
  4. washwashed twice with water (30 ml
  5. concentrationThe organic phase is concentrated
  6. temperaturewith heat to about 30 ml
  7. customwith crystals forming as the solution cools
  8. temperatureThe mixture is cooled to 0°-5°
  9. filtrationfiltered
  10. washwashed with a minimum amount of heptane
  11. customdried at 70°

出典と根拠

ORDレコード
ord-833163a22a864aeb9e9397e1b01d537d
出典データセット
uspto-grants-1990_10
特許番号
USRE033364

関連ノート

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