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

HRID 1168057Notes

Reaction equation

HRID 1168057 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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%).

Workup

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

Sources & evidence

ORD record
ord-190c0ef1b326424ba945d125d7ea9bfb
Source dataset
uspto-grants-2003_09
Patent number
US06620977B1

Reaction notes

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