Methanesulfonyl chloride → HCID 15391547、化合物

HRID 54024ノート

反応式

HRID 54024 の反応式
[OH:1][CH2:2][CH2:3][O:4][CH2:5][CH:6]([CH2:26][CH2:27][OH:28])[CH2:7][O:8][Si:9]([C:22]([CH3:25])([CH3:24])[CH3:23])([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[CH3:29][S:30](Cl)(=[O:32])=[O:31]>C(Cl)Cl.CCOCC>[CH3:29][S:30]([O:1][CH2:2][CH2:3][O:4][CH2:5][CH:6]([CH2:26][CH2:27][O:28][S:30]([CH3:29])(=[O:32])=[O:31])[CH2:7][O:8][Si:9]([C:22]([CH3:24])([CH3:23])[CH3:25])([C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)(=[O:32])=[O:31]

参加物

5

反応物 2

HCID 31297Methanesulfonyl chlorideHCID 187904721-(2-Hydroxyethoxy)-2-(2-hydroxyethyl)-3-(tert-butyldiphenylsilyloxy)-propane

生成物 1

HCID 15391547HCID 15391547、化合物収率 97.4%

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 6344Dichloromethane溶媒2 回

実験手順

To a stirred CH2Cl2 (400 mL) solution of diol, 1-(2-hydroxyethoxy)-2-(2-hydroxyethyl)-3-(tert-butyldiphenylsilyloxy)-propane (5.48 g, 13.6 mmol) under N2 atmosphere was added TEA (11.2 mL, 78 mmol), followed by dropwise addition of methane sulfonyl chloride (3 mL, 39.00 mmol) in CH2Cl2 (100 mL) over a period of 30 minutes. After 12 hours, the reaction was diluted with ether (500 mL), washed with water (100 mL×3), brine (100 mL), dried, and concentrated under reduced pressure to a residue. The residue was eluted through a short silica gel column with ethyl acetate/hexane (10% to 50% ethyl acetate gradient) and evaporation of the eluting solvent gave the bismesylate, 1-(2-(methylsulfonyloxy)-ethoxy)-2-((methylsulfonyloxy)ethyl)-3-(tert-butyldiphenylsilyloxy)-propane (7.40 g, 97%). Rf =0.55 (50% ethyl acetate in hexane). NMR. ##STR24##

後処理

  1. washwashed with water (100 mL×3), brine (100 mL)
  2. customdried
  3. concentrationconcentrated under reduced pressure to a residue
  4. washThe residue was eluted through a short silica gel column with ethyl acetate/hexane (10% to 50% ethyl acetate gradient) and evaporation of the eluting solvent

出典と根拠

ORDレコード
ord-3013e1b1ad34469cb9016151d3451817
出典データセット
uspto-grants-1997_04
特許番号
US05621098

反応ノート

読み込み中…