Ammonium Chloride → (S)-3-(2-hydroxyethoxy)-4-trityloxybutanol

HRID 1168057노트

반응식

HRID 1168057 반응식
[Si]([O:8][CH2:9][CH2:10][C@H:11]([O:33][CH2:34][CH2:35][O:36][Si](C(C)(C)C)(C)C)[CH2:12][O:13][C:14]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[Cl-].[NH4+]>O1CCCC1>[OH:36][CH2:35][CH2:34][O:33][C@H:11]([CH2:12][O:13][C:14]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)([C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)[CH2:10][CH2:9][OH:8]

참가 물질

5

반응물 3

HCID 25517Ammonium ChlorideHCID 2724141Tetrabutylammonium FluorideHCID 12114687(S)-4-tert-butyldimethylsilyloxy-2-(2-tert-butyldimethylsilyloxyethoxy)-1-trityloxybutane

생성물 1

HCID 10786707(S)-3-(2-hydroxyethoxy)-4-trityloxybutanol수율 76.9%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To (S)-4-tert-butyldimethylsilyloxy-2-(2-tert-butyldimethylsilyloxyethoxy)-1-trityloxybutane (32 mg, 0.053 mmol) in dried tetrahydrofuran (THF) (2 ml) was added tetrabutylammonium fluoride (0.10 ml, 0.11 mmol, 1.1 M in THF) and the mixture was stirred for 1.5 hours at room temperature. A small amount of saturated ammonium chloride was added to the reaction mixture. The solution was dried on sodium sulfate, filtered and condensed in vacuo. The residue was subjected to silica gel chromatography to give (S)-3-(2-hydroxyethoxy)-4-trityloxybutanol (16 mg, yield 75%).

후처리

  1. customThe solution was dried on sodium sulfate
  2. filtrationfiltered
  3. customcondensed in vacuo

출처 및 근거

ORD 기록
ord-190c0ef1b326424ba945d125d7ea9bfb
출처 데이터셋
uspto-grants-2003_09
특허 번호
US06620977B1

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