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

HRID 231256
ノート
印刷プレビュー

反応式

HRID 231256 の反応式
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]
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

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

生成物 1

HCID 145010382-Methoxy-3-octadecyloxypropyl 6-hydroxyhexyl sulfide収率 97.5%

試薬・触媒・溶媒 3

HCID 887
Methanol
溶媒
HCID 962Water溶媒
HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-4c91898a85ad49d3857d98c9dbfe87a3
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

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