Water → methyl (S)-8-(benzyloxy)-4-(2-hydroxyethyl)octanoate

HRID 465625ノート

反応式

HRID 465625 の反応式
[CH2:1]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][C@H:13]([CH2:20][CH:21]=[O:22])[CH2:14][CH2:15][C:16]([O:18][CH3:19])=[O:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+].O.C(=O)(O)[O-].[Na+]>C(O)C>[CH2:1]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][C@H:13]([CH2:20][CH2:21][OH:22])[CH2:14][CH2:15][C:16]([O:18][CH3:19])=[O:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

6

反応物 4

HCID 962WaterHCID 516892Sodium BicarbonateHCID 4311764Sodium borohydrideHCID 10357812methyl (S)-8-(benzyloxy)-4-(formylmethyl)octanoate

生成物 1

HCID 10380582methyl (S)-8-(benzyloxy)-4-(2-hydroxyethyl)octanoate

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

To a solution of the crude methyl (S)-8-(benzyloxy)-4-(formylmethyl)octanoate (2.44 g crude) in ethanol (22 ml) is added sodium borohydride (0.307 g, 8.1 mmol). The reaction is stirred for 15 minutes and then poured into water. The pH of the mixture is adjusted to 8.0 using saturated sodium bicarbonate solution. The mixture is extracted with methylene chloride (3×30 ml) and the combined organic extracts are dried, filtered and evaporated to give an oil. This is purified by flash chromatography on silica gel using 1:1 ethyl acetate/hexane as eluent to yield methyl (S)-8-(benzyloxy)-4-(2-hydroxyethyl)-octanoate (oil), [alpha]D25 -1.22° (c 1.02 in methanol).

後処理

  1. extractionThe mixture is extracted with methylene chloride (3×30 ml)
  2. customthe combined organic extracts are dried
  3. filtrationfiltered
  4. customevaporated
  5. customto give an oil
  6. customThis is purified by flash chromatography on silica gel using 1:1 ethyl acetate/hexane as eluent

出典と根拠

ORDレコード
ord-c34269d5450540fbb4a489cb196d0ddb
出典データセット
uspto-grants-1992_10
特許番号
US05153214

反応ノート

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