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

HRID 1168057Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1168057
[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]

Komponenten

5

Edukt 3

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

Produkt 1

HCID 10786707(S)-3-(2-hydroxyethoxy)-4-trityloxybutanolAusbeute 76,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

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%).

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-190c0ef1b326424ba945d125d7ea9bfb
Quelldatensatz
uspto-grants-2003_09
Patentnummer
US06620977B1

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