Hydrochloric Acid → 17beta-Allyloxy-13-ethyl-3-methoxygona-1,3,5(10)-triene

HRID 1077245

반응식

HRID 1077245 반응식
[CH2:1]([C@:3]12[CH2:11][CH2:10][C@@H:9]3[C:12]4[CH:13]=[CH:14][C:15]([O:20][CH3:21])=[CH: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].[H-].[Na+].[CH2:25](Br)[CH:26]=[CH2:27].Cl>C1(C)C(C)=CC=CC=1>[C:26]([O:22][CH:4]1[C@:3]2([CH2:1][CH3:2])[C@H:7]([C@@H:8]3[CH2:19][CH2:18][C:17]4[CH:16]=[C:15]([O:20][CH3:21])[CH:14]=[CH:13][C:12]=4[C@H:9]3[CH2:10][CH2:11]2)[CH2:6][CH2:5]1)(=[CH2:25])[CH3:27]

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 7841Allyl bromideHCID 24758Sodium hydrideHCID 66432(17beta)-13-Ethyl-3-methoxygona-1,3,5(10)-trien-17-ol

생성물 1

HCID 8673349217beta-Allyloxy-13-ethyl-3-methoxygona-1,3,5(10)-triene

시약·촉매·용매 1

HCID 7237O-Xylene용매

실험 절차

Reflux a suspension of 5.0 g. of dl-13-ethyl-3-methoxygona-1,3,5(10)-triene-17β-ol, 100 mg. of xylene, and 3.9 g. of sodium hydride (50% in mineral oil) for 1.5 hours. Add 14.5 ml. of allyl bromide and reflux for 22 hours. Make the reaction mixture acidic with dilute hydrochloric acid and extract the organic layer with sodium bicarbonate solution. Chromatograph the residue on alumina (Grade I neutral) in hexane and eluate the product with ether to obtain dl-17β-allyloxy-13-ethyl-3-methoxygona-1,3,5(10)-triene.

후처리

  1. temperatureReflux
  2. additiona suspension of 5.0 g
  3. additionAdd 14.5 ml
  4. extractionextract the organic layer with sodium bicarbonate solution

출처 및 근거

ORD 기록
ord-db1a331c08994f5382dc45e5bb1d0a9b
출처 데이터셋
uspto-grants-1976_05
특허 번호
US03959322

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