tert-Butyldimethylsilyl chloride → HCID 22406983, compound

HRID 440336Notes

Reaction equation

HRID 440336 reaction equation
[OH:1][CH:2]([C:8]1[S:9][CH:10]=[CH:11][N:12]=1)[CH2:3][O:4][CH2:5][O:6][CH3:7].[CH3:13][C:14]([Si:17](Cl)([CH3:19])[CH3:18])([CH3:16])[CH3:15].C1CCN2C(=NCCC2)CC1>C1COCC1.O>[O:1]([CH:2]([C:8]1[S:9][CH:10]=[CH:11][N:12]=1)[CH2:3][O:4][CH2:5][O:6][CH3:7])[Si:17]([C:14]([CH3:16])([CH3:15])[CH3:13])([CH3:19])[CH3:18]

Participants

6

Reactant 3

HCID 28928tert-Butyldimethylsilyl chlorideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 22406940HCID 22406940, compound

Product 1

HCID 22406983HCID 22406983, compoundYield 70.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 2-(1-hydroxy-2-(methoxymethoxy)ethyl)thiazole (0.93 mmol, 0.18 g), TBSCl (1.1 mmol, 0.17 g) and DBU (1.1 mmol, 0.16 mL) in THF (1 mL) was stirred at rt overnight. The reaction was diluted with water and extracted with ethyl ether, dried (MgSO4), filtered and concentrated. The residue was subjected to flash chromatography (10% ethyl acetate/hexane) to afford 0.20 g (70%) of 2-(1-(t-butyldimethylsiloxy)-2-(methoxymethoxy)ethyl)thiazole.

Workup

  1. extractionextracted with ethyl ether
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-f989527eb93e4b02a597a9b1311a877c
Source dataset
uspto-grants-1996_05
Patent number
US05519040

Reaction notes

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