Hydrochloric Acid → Estra-1,3,5(10),7-tetraene-3,17alpha-diol diacetate

HRID 1701933ノート

反応式

HRID 1701933 の反応式
[CH3:1][C@@:2]12[C@H:19]([OH:20])[CH2:18][CH2:17][C@H:16]1[C:6]1=[CH:7][CH2:8][C:9]3[CH:14]=[C:13]([OH:15])[CH:12]=[CH:11][C:10]=3[C@H:5]1[CH2:4][CH2:3]2.[C:21]1([CH3:31])C=CC(S(O)(=O)=O)=CC=1.[C:32](OC(=O)C)(=[O:34])[CH3:33].Cl.[OH2:40]>N1C=CC=CC=1>[C:32]([O:15][C:13]1[CH:12]=[CH:11][C:10]2[C@@H:5]3[C:6]([C@H:16]4[C@@:2]([CH2:3][CH2:4]3)([CH3:1])[C@H:19]([O:20][C:21](=[O:40])[CH3:31])[CH2:18][CH2:17]4)=[CH:7][CH2:8][C:9]=2[CH:14]=1)(=[O:34])[CH3:33]

参加物

7

反応物 5

HCID 313Hydrochloric AcidHCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 7918Acetic AnhydrideHCID 9547222alpha-Dihydroequilin2 回

生成物 1

HCID 6454273Estra-1,3,5(10),7-tetraene-3,17alpha-diol diacetate

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

反応条件

温度
60 °C

実験手順

17α-Dihydroequilin (1 g), p-toluenesulfonic acid (1 g), and acetic anhydride (40 ml) were heated in an oil bath at 100° C. until a clear solution was obtained and then left at room temperature in the dark for 2 days. At this time TLC showed no detectable amount of 17α-dihydroequilin. The mixture was poured into a solution of pyridine (30 ml) and water (400 ml), acidified with 4 N hydrochloric acid and extracted with diethyl ether (300 ml). The ether phase was washed with water (150 ml) and evaporated to dryness in vacuo. The product was dissolved in methanol (75 ml), heated to 60° C. and water (40 ml) added. After cooling, 1.14 g of 1,3,5(10),7-estratetraene-3,17α-diol 3,17-diacetate was obtained, m.p. 124°-126° C.

後処理

  1. customwas obtained
  2. extractionextracted with diethyl ether (300 ml)
  3. washThe ether phase was washed with water (150 ml)
  4. customevaporated to dryness in vacuo
  5. dissolutionThe product was dissolved in methanol (75 ml)
  6. additionwater (40 ml) added
  7. temperatureAfter cooling

出典と根拠

ORDレコード
ord-d9d09e4b9e48433e81cc4c1cdd58b353
出典データセット
uspto-grants-1983_04
特許番号
US04379780

反応ノート

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