Bicarbonate Ion → 7alpha-(5-Chloropentyl)-estr-4-ene-3,17-dione

HRID 1603344노트

반응식

HRID 1603344 반응식
O[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C@@H:7]1[CH2:24][C:23]2[C@H:18]([CH2:19][CH2:20][C:21](=[O:25])[CH:22]=2)[C@@H:17]2[C@@H:8]1[C@H:9]1[C@@:13]([CH2:15][CH2:16]2)([CH3:14])[C:12](=[O:26])[CH2:11][CH2:10]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(=O)(O)[O-].C(Cl)(Cl)(Cl)[Cl:51]>C(#N)C.ClCCl>[Cl:51][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C@@H:7]1[CH2:24][C:23]2[C@H:18]([CH2:19][CH2:20][C:21](=[O:25])[CH:22]=2)[C@@H:17]2[C@@H:8]1[C@H:9]1[C@@:13]([CH2:15][CH2:16]2)([CH3:14])[C:12](=[O:26])[CH2:11][CH2:10]1

참가 물질

7

반응물 4

HCID 769Bicarbonate IonHCID 5943Carbon TetrachlorideHCID 11776TriphenylphosphineHCID 158381567a-(5-Hydroxypentyl)-estr-4-ene-3,17-dione

생성물 1

HCID 571565697alpha-(5-Chloropentyl)-estr-4-ene-3,17-dione

시약·촉매·용매 2

HCID 6342Acetonitrile용매HCID 6344Dichloromethane용매

실험 절차

The same product is obtained from 8.05 g of 7α-(5-hydroxypentyl)-estr-4-ene-3,17-dione (Example 1b) by a 3.5-hour reaction with 8.66 g of triphenylphosphine in 85 ml of carbon tetrachloride and 30 ml of acetonitrile at room temperature. The reaction mixture is diluted with dichloromethane, shaken out with saturated bicarbonate solution and with saturated common salt solution, dried with sodium sulfate and concentrated by evaporation in a vacuum. The residue is chromatographed on silica gel with dichloromethane and ethyl acetate, whereby 4.08 g of 7α-(5-chloropentyl)-estr-4-ene-3,17-dione is obtained, [α]D22 =+68° (c=0.5% in chloroform)

후처리

  1. dry with materialdried with sodium sulfate
  2. concentrationconcentrated by evaporation in a vacuum
  3. customThe residue is chromatographed on silica gel with dichloromethane and ethyl acetate

출처 및 근거

ORD 기록
ord-b8814bb9882646888a75d848d10a4d25
출처 데이터셋
uspto-grants-1999_11
특허 번호
US05986115

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