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

HRID 231275
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인쇄 미리보기

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HRID 231275 반응식
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]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 887Methanol
용매
HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-bacae9d55f0144cdbdc047a7c7c98359
출처 데이터셋
uspto-grants-1989_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04845219

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