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Thioguaiacol → HCID 21055320、化合物

HRID 2215270
ノート
印刷プレビュー

反応式

HRID 2215270 の反応式
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[SH:9].[H-].[Na+].C1(C)C=CC(S([O:21][CH2:22][C@@H:23]([CH2:26][CH3:27])[CH2:24]O)(=O)=O)=CC=1>CN(C)C=O>[CH2:26]([C@H:23]([CH2:24][S:9][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=1[O:2][CH3:1])[CH2:22][OH:21])[CH3:27]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 23642ThioguaiacolHCID 24758Sodium hydrideHCID 21055323HCID 21055323、化合物

生成物 1

HCID 21055320HCID 21055320、化合物収率 100%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒3 回

反応条件

温度
0 °C

実験手順

0.47 ml (0.0038 mol) of 2-methoxythiophenol, in solution in 5 ml of dimethylformamide, is added dropwise to a round-bottomed flask, kept under an inert atmosphere, comprising 0.19 g (0.0047 mol) of sodium hydride in suspension in 10 ml of dimethylformamide cooled to 0° C. The mixture is reheated to ambient temperature and stirred for 1 hour, then 0.99 g (0.0038 mol) of 2-(S)-ethyl-3-hydroxypropyl p-toluene-sulfonate (XIXd-1), in solution in 10 ml of dimethyl-formamide, is added. After stirring at ambient temperature for 2 hours, the dimethylformamide is evaporated under high vacuum and the residue is taken up in dichloromethane. The organic phase is washed with water and with brine, dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue is purified by flash chromatography on silica gel (eluent: dichloromethane/methanol=98:2). 0.87 g (0.0038 mol) of the title compound (XXd-1) is recovered in the form of an oil.

後処理

  1. customis reheated to ambient temperature
  2. stirringAfter stirring at ambient temperature for 2 hours
  3. customthe dimethylformamide is evaporated under high vacuum
  4. washThe organic phase is washed with water and with brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue is purified by flash chromatography on silica gel (eluent: dichloromethane/methanol=98:2)

出典と根拠

ORDレコード
ord-100010604e0e4f21884f198001f55dc5
出典データセット
uspto-grants-2006_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07109234B2

反応ノート

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