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

HRID 1168057ノート

反応式

HRID 1168057 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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%).

後処理

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

出典と根拠

ORDレコード
ord-190c0ef1b326424ba945d125d7ea9bfb
出典データセット
uspto-grants-2003_09
特許番号
US06620977B1

反応ノート

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