Ammonium Chloride → 2-[1-[[2-(Trimethylsilyl)ethoxy]methoxy]cyclobutyl]thiazole
Reaction equation
[OH:1][C:2]1([C:6]2[S:7][CH:8]=[CH:9][N:10]=2)[CH2:5][CH2:4][CH2:3]1.CCN(C(C)C)C(C)C.[CH3:20][Si:21]([CH3:28])([CH3:27])[CH2:22][CH2:23][O:24][CH2:25]Cl.[NH4+].[Cl-]>ClCCl>[CH3:20][Si:21]([CH3:28])([CH3:27])[CH2:22][CH2:23][O:24][CH2:25][O:1][C:2]1([C:6]2[S:7][CH:8]=[CH:9][N:10]=2)[CH2:5][CH2:4][CH2:3]1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a solution of the alcohol 2-[(1-Hydroxy)cyclobutyl]thiazole from Step 1 (5 g, 32 mmol) and Hunig's base (10.4 mL, 60 mmol) in dichloromethane (100 mL) at 0° C. was added 2-(trimethylsilyl)ethoxymethyl chloride (6.5 mL, 36.7 mmol). The resulting solution was stirred at 0° C. for 1 h, was heated at reflux temperature for 3.5 h and finally was stirred at room temperature for 15 h. Sat. aq. NH4Cl was added and the resulting mixture was extracted with dichloromethane (3×). The combined organics were washed with water, brine, dried (MgSO4) and concentrated. Flash chromatography of-the residue (silica gel; dichloromethane to dichloromethane/ethyl acetate 95:5) provided 2-{1-[(2-Trimethylsilylethoxy)methoxy]cyclobutyl}thiazole (2 g).
Workup
- temperaturewas heated
- temperatureat reflux temperature for 3.5 h
- stirringfinally was stirred at room temperature for 15 h
- extractionthe resulting mixture was extracted with dichloromethane (3×)
- washThe combined organics were washed with water, brine
- dry with materialdried (MgSO4)
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-99a2f61b0e2e4650a0013d4e0eb5ade8
- Source dataset
- uspto-grants-2005_01
- Patent number
- US06841564B2
Reaction notes
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