6-Mercapto-1-hexanol → 2-Methoxy-3-octadecyloxypropyl 6-hydroxyhexyl sulfide

HRID 231256

반응식

HRID 231256 반응식
C[O-].[Na+].[SH:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][OH:11].[BH4-].[Na+].CS(O[CH2:19][CH:20]([O:41][CH3:42])[CH2:21][O: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][CH2:38][CH2:39][CH3:40])(=O)=O>O.C1COCC1.CO>[OH:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][S:4][CH2:19][CH:20]([O:41][CH3:42])[CH2:21][O: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][CH2:38][CH2:39][CH3:40]

참가 물질

8

반응물 4

HCID 5601266-Mercapto-1-hexanolHCID 4311764Sodium borohydrideHCID 10942334Sodium MethoxideHCID 145010372-Methoxy-3-octadecyloxypropyl methanesulfonate

생성물 1

HCID 145010382-Methoxy-3-octadecyloxypropyl 6-hydroxyhexyl sulfide수율 97.5%

시약·촉매·용매 3

HCID 887Methanol용매HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

To 14 ml of a methanol solution of sodium methoxide (1M solution) are added 2.04 g of 6-mercaptohexanol and 0.24 g of sodium borohydride, to which a THF (20 ml) solution containing 2.18 g of 2-methoxy-3-octadecyloxypropyl methanesulfonate is added dropwise under nitrogen streams with stirring. The mixture is stirred at room temperature for 20 hours and then at 40° C. for 1 hour. After the addition of water, the mixture is extracted with ethyl acetate. The extracted layer is washed with water, dried and concentrated under reduced pressures to obtain an oily product. Purification of the oily product by silica gel column chromatography gives 2.31 g of the captioned compound.

후처리

  1. additionis added dropwise under nitrogen streams
  2. stirringThe mixture is stirred at room temperature for 20 hours
  3. extractionthe mixture is extracted with ethyl acetate
  4. washThe extracted layer is washed with water
  5. customdried
  6. concentrationconcentrated under reduced pressures
  7. customto obtain an oily product
  8. customPurification of the oily product by silica gel column chromatography

출처 및 근거

ORD 기록
ord-4c91898a85ad49d3857d98c9dbfe87a3
출처 데이터셋
uspto-grants-1989_07
특허 번호
US04845219

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