Water → 3-(Hexadecyloxy)-2-(hexadecylthio)methyl-1-propanol

HRID 248167ノート

反応式

HRID 248167 の反応式
[BH4-].[Li+].[CH2:3]([O:19][CH2:20][CH:21]([CH2:27][S:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH3:44])[C:22](OCC)=[O:23])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].O>O1CCCC1>[CH2:3]([O:19][CH2:20][CH:21]([CH2:27][S:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH3:44])[CH2:22][OH:23])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]

参加物

5

反応物 3

HCID 962WaterHCID 4148881Lithium borohydrideHCID 19764340Ethyl 3-(hexadecyloxy)-2-[(hexadecylthio)methyl]propanoate

生成物 1

HCID 197643273-(Hexadecyloxy)-2-(hexadecylthio)methyl-1-propanol収率 68.1%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a slurry of 1.04 g of lithium borohydride in tetrahydrofuran at ambient temperature is added 29 g of ethyl 3-(hexadecyloxy)-2-[(hexadecylthio)methyl]propanoate followed by heating at reflux for 18 hours. The mixture is poured into water containing a small amount of acid followed by extraction with ether to give after drying and evaporation, a residue which is columned on silica gel using 30:1 hexane:ethyl acetate. Fractions containing the product are evaporated to give 18.4 g of the desired product.

後処理

  1. temperatureby heating
  2. temperatureat reflux for 18 hours
  3. extractionfollowed by extraction with ether
  4. customto give
  5. customafter drying
  6. customevaporation
  7. additionFractions containing the product
  8. customare evaporated

出典と根拠

ORDレコード
ord-d8b570829fa441559ec8c2e3fe9e9268
出典データセット
uspto-grants-1993_05
特許番号
US05208223

反応ノート

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