Hydrochloric Acid → Gon-4-en-3-one, 13-ethyl-17-hydroxy-, (17beta)-(+-)-

HRID 1077180

反応式

HRID 1077180 の反応式
[CH2:1]([C@:3]12[CH2:11][CH2:10][C@@H:9]3[C:12]4[CH2:13][CH:14]=[C:15]([O:20]C)[CH2:16][C:17]=4[CH2:18][CH2:19][C@H:8]3[C@@H:7]1[CH2:6][CH2:5][C@@H:4]2[OH:22])[CH3:2].Cl.O.CCOCC>CO>[CH2:1]([C@:3]12[CH2:11][CH2:10][C@@H:9]3[C@@H:12]4[C:17]([CH2:18][CH2:19][C@H:8]3[C@@H:7]1[CH2:6][CH2:5][C@@H:4]2[OH:22])=[CH:16][C:15](=[O:20])[CH2:14][CH2:13]4)[CH3:2]

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 3283Diethyl EtherHCID 101950(17Beta)-13-Ethyl-3-methoxygona-2,5(10)-dien-17-ol

生成物 1

HCID 10039774Gon-4-en-3-one, 13-ethyl-17-hydroxy-, (17beta)-(+-)-

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

Dissolve 13β-ethyl-3-methoxy-gona-2,5(10)-dien-17β-ol (0.47 g.) in hot methanol (25 cc.). Add 3N hydrochloric acid (15 cc.) and keep the mixture at 70° C. under nitrogen for 1 hour. Add water and work up with ether and chromatograph the resulting gum on activated alumina (40 g.). Elute with ether to give a fraction (0.2 g.) which on recrystallization from light petroleum gives 13β-ethyl-17β-hydroxy-gon-4-en-3-one; m.p. 153°-5° C; ultra-violet absorption peak at 240 mμ (ε 16,300).

後処理

  1. customat 70° C.
  2. customfor 1 hour
  3. washElute with ether
  4. customto give a fraction (0.2 g.) which
  5. customon recrystallization from light petroleum

出典と根拠

ORDレコード
ord-1a5af62c81a946a696728be7a323e44c
出典データセット
uspto-grants-1976_05
特許番号
US03959322

関連ノート

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