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

HRID 465625노트

반응식

HRID 465625 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-c34269d5450540fbb4a489cb196d0ddb
출처 데이터셋
uspto-grants-1992_10
특허 번호
US05153214

반응 노트

불러오는 중…