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

HRID 1701933노트

반응식

HRID 1701933 반응식
[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]

참가 물질

7

반응물 5

HCID 313Hydrochloric AcidHCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 7918Acetic AnhydrideHCID 9547222alpha-Dihydroequilin2회

생성물 1

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

시약·촉매·용매 1

HCID 1049Pyridine용매

반응 조건

온도
60 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-d9d09e4b9e48433e81cc4c1cdd58b353
출처 데이터셋
uspto-grants-1983_04
특허 번호
US04379780

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