Triethylamine → HCID 67739305、化合物

HRID 2225360ノート

反応式

HRID 2225360 の反応式
[C:1]([O:4][C@H:5]1[CH2:10][CH2:9][C@H:8]2[C@H:11]3[C@H:20]([CH2:21][CH2:22][C@:6]12[CH3:7])[C@@H:19]1[C@H:14]([CH2:15][C:16](=[O:23])[CH2:17][CH2:18]1)[CH2:13][CH2:12]3)(=[O:3])[CH3:2].C(N(CC)CC)C.O([Si:39]([C:42]([CH3:45])([CH3:44])[CH3:43])([CH3:41])[CH3:40])S(C(F)(F)F)(=O)=O>ClCCl>[C:1]([O:4][C@H:5]1[CH2:10][CH2:9][C@H:8]2[C@H:11]3[C@H:20]([CH2:21][CH2:22][C@:6]12[CH3:7])[C@@H:19]1[C@H:14]([CH2:15][CH:16]([O:23][Si:39]([C:42]([CH3:45])([CH3:44])[CH3:43])([CH3:41])[CH3:40])[CH2:17][CH2:18]1)[CH2:13][CH2:12]3)(=[O:3])[CH3:2]

参加物

5

反応物 3

HCID 8471TriethylamineHCID 123564tert-Butyldimethylsilyl trifluoromethanesulphonateHCID 24213233767-87-2

生成物 1

HCID 67739305HCID 67739305、化合物収率 87.4%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

To a solution of 17β-acetyloxy-5α-estran-3-one (1.595 g, 5 mmol) in dry dichloromethane (30 mL) was added with stirring at ice-water bath temperature, triethyl amine (2 mL) followed by t-butyldimethylsilyl triflate (2.64 g, 10 mmol). The solution was stirred for 25 min, then diluted with dichloromethane (20 mL) and washed with satd.aq. NaHCO3 (30 mL), brine (30 mL) and dried over Na2SO4. The solvent was removed to yield a solid, which was purified by chromatography (silica gel, dichloromethane, pretreated with 1% triethyl amine in hexanes) to get 1.9 g (87%) of pure product as colorless crystals, m.p. 89°-90° C.

後処理

  1. washwashed with satd.aq
  2. dry with materialNaHCO3 (30 mL), brine (30 mL) and dried over Na2SO4
  3. customThe solvent was removed
  4. customto yield a solid, which
  5. customwas purified by chromatography (silica gel, dichloromethane, pretreated with 1% triethyl amine in hexanes)

出典と根拠

ORDレコード
ord-f7fe9fdcc0084dbeab49b9c1c15ea95b
出典データセット
uspto-grants-1994_09
特許番号
US05344826

反応ノート

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