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

HRID 7412

反応式

HRID 7412 の反応式
[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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 241Benzene溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-faa2f348d6f5478eb5c5bd468fd5e72f
出典データセット
uspto-grants-2006_08
特許番号
US07087590B2

関連ノート

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