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4-Sulfanylbutan-1-ol → 2-Methoxy-3-octadecyloxypropyl 4-hydroxybutyl sulfide

HRID 231275
ノート
印刷プレビュー

反応式

HRID 231275 の反応式
C[O-].[Na+].[SH:4][CH2:5][CH2:6][CH2:7][CH2:8][OH:9].[BH4-].[Na+].CS(O[CH2:17][CH:18]([O:39][CH3:40])[CH2:19][O:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH3:38])(=O)=O>O1CCCC1.CO>[OH:9][CH2:8][CH2:7][CH2:6][CH2:5][S:4][CH2:17][CH:18]([O:39][CH3:40])[CH2:19][O:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH3:38]
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 5482614-Sulfanylbutan-1-olHCID 4311764Sodium borohydrideHCID 10942334Sodium MethoxideHCID 145010372-Methoxy-3-octadecyloxypropyl methanesulfonate

生成物 1

HCID 539416312-Methoxy-3-octadecyloxypropyl 4-hydroxybutyl sulfide

試薬・触媒・溶媒 2

HCID 887Methanol
溶媒
HCID 8028Tetrahydrofuran溶媒

実験手順

To 40 ml of a methanol solution of sodium methoxide (1 M solution) are added 3.1 g of 4-mercaptobutanol and 0.5 g of sodium borohydride, to which is added dropwise a solution of 4.36 g of 2-methoxy-3-octadecyloxypropyl methanesulfonate in 40 ml of tetrahydrofuran at room temperature with stirring. The mixture is stirred at room temperature for 14 hours and then at 40° C. for 1.5 hours. The solvent is distilled off under reduced pressure and the residue is acidified with hydrochloric acid and extracted with hexane. The extract layer is washed with water, dried and concentrated to leave crude 2-methoxy-3-octadecyloxypropyl 4-hydroxybutyl sulfide. This sulfide is dissolved in 75 ml of dichlromethane, to which 7.6 g of m-chloroperbenzoic acid is added little by little at room temperature with stirring. The mixture is then stirred at room temperature for 1 hour and is filtered to remove precipitates. The filtrate is washed with an aqueous sodium sulfite solution, an aqueous sodium bicarbonate solution and water, dried and concentrated to leave a residue which in turn is purified by silica gel column chromatography to obtain 2.5 g of the captioned compound.

後処理

  1. stirringThe mixture is stirred at room temperature for 14 hours
  2. distillationThe solvent is distilled off under reduced pressure
  3. extractionextracted with hexane
  4. washThe extract layer is washed with water
  5. customdried
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-bacae9d55f0144cdbdc047a7c7c98359
出典データセット
uspto-grants-1989_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US04845219

反応ノート

読み込み中…

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