Ethylene Glycol → 3-Hydroxy-5beta-estran-17-one ethylene ketal

HRID 7412

반응식

HRID 7412 반응식
[OH:1][CH:2]1[CH2:19][CH2:18][C@H:17]2[C@H:4]([CH2:5][CH2:6][C@@H:7]3[C@@H:16]2[CH2:15][CH2:14][C@@:12]2([CH3:13])[C@H:8]3[CH2:9][CH2:10][C:11]2=[O:20])[CH2:3]1.[CH2:21](O)[CH2:22][OH:23].C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1.CCOC(C)=O.CCCCCC>C1C=CC=CC=1.CCOC(C)=O>[CH2:22]1[O:23][C:11]2([CH2:10][CH2:9][C@H:8]3[C@H:7]4[C@H:16]([CH2:15][CH2:14][C@:12]23[CH3:13])[C@@H:17]2[C@@H:4]([CH2:3][CH:2]([OH:1])[CH2:19][CH2:18]2)[CH2:5][CH2:6]4)[O:20][CH2:21]1

참가 물질

7

반응물 4

HCID 174Ethylene GlycolHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 21226206Ethyl acetate hexaneHCID 227956593-Hydroxy-5betaestran-17-one

생성물 1

HCID 867601793-Hydroxy-5beta-estran-17-one ethylene ketal수율 94.8%

시약·촉매·용매 2

HCID 241Benzene용매HCID 8857Ethyl Acetate용매

실험 절차

Compound 4(10 g, 36.2 mmol) was dissolved in dry benzene (150 ml) mixed with ethylene glycol (25 ml, 280 mmol) and pyridinium p-toluenesulfonate (1 g, 3.9 mmol) and refluxed using a Dean-stark separator overnight till no starting material was detected by TLC. The cold solution was diluted with EtOAc (100 ml), washed twice with brine, dried on Na2SO4 and the solvents removed under reduced pressure. Flash-chromatography on silica gel with EtOAc: Hexane 4:6 as eluant to give 11.0 g (94.5% yield) the title compound as a white solid.

후처리

  1. temperaturerefluxed
  2. washwashed twice with brine
  3. customdried on Na2SO4
  4. customthe solvents removed under reduced pressure

출처 및 근거

ORD 기록
ord-faa2f348d6f5478eb5c5bd468fd5e72f
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07087590B2

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