Acetic Acid → (S)-1-trityloxy-2,4-butanediol

HRID 1168054노트

반응식

HRID 1168054 반응식
[OH:1][C@H:2]([CH2:9][O:10][C:11]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH2:3][C:4](OCC)=[O:5].[BH4-].[Na+].C(O)(=O)C>C(O)C.O>[C:11]([O:10][CH2:9][C@@H:2]([OH:1])[CH2:3][CH2:4][OH:5])([C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

참가 물질

6

반응물 3

HCID 176Acetic AcidHCID 4311764Sodium borohydrideHCID 10883658(S)-ethyl 3-hydroxy-4-trityloxybutanoate

생성물 1

HCID 14027585(S)-1-trityloxy-2,4-butanediol수율 82.4%

시약·촉매·용매 2

HCID 702Ethanol용매HCID 962Water용매

실험 절차

In ethanol (10 ml) was dissolved (S)-ethyl 3-hydroxy-4-trityloxybutanoate (0.37 g, 0.975 mmol). Sodium borohydride (0.238 g, 6.29 mmol) was added to the solution and the solution was stirred at room temperature over night. Acetic acid was added to neutralize the solution. The solution was diluted with water (100 ml) and extracted with ethyl acetate. The extract was washed with saturated brine, dried on magnesium sulfate, filtered, and condensed in vacuo. The residue was subjected to silica gel chromatography to give (S)-1-trityloxy-2,4-butanediol (0.28 g, yield 82%).

후처리

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. customdried on magnesium sulfate
  4. filtrationfiltered
  5. customcondensed in vacuo

출처 및 근거

ORD 기록
ord-77054286635e455885abdad53fd3a3b7
출처 데이터셋
uspto-grants-2003_09
특허 번호
US06620977B1

반응 노트

불러오는 중…