Nitrogen → (2-(2-Methoxypropan-2-yl)oxazol-4-yl)methanol
Reaction equation
N#N.[Si]([O:10][CH2:11][C:12]1[N:13]=[C:14]([C:17]([O:20][CH3:21])([CH3:19])[CH3:18])[O:15][CH:16]=1)(C(C)(C)C)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1.CC(=O)OCC>[CH3:21][O:20][C:17]([C:14]1[O:15][CH:16]=[C:12]([CH2:11][OH:10])[N:13]=1)([CH3:19])[CH3:18]Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 0 °C
Procedure
In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of 4-(((tert-butyldimethylsilyl)oxy)methyl)-2-(2-methoxypropan-2-yl)oxazole (110 mg, 0.39 mmol) in THF (1.8 mL) was treated at 0° C. with TBAF (0.39 mL of a 1M solution in THF, 0.39 mmol) and the resulting mixture was stirred for 45 min at 0° C. The reaction mixture was diluted with EA (10 mL), washed with sat. aq. NH4Cl (5 mL) and brine, dried over MgSO4, filtered and the solvent was removed under reduced pressure. Purification of the residue by FC (3:7 hept-EA) gave the title compound as a yellow oil: TLC: rf (3:7 hept-EA)=0.20. LC-MS-conditions 07: tR=0.44 min, [M+H]+=172.01.
Workup
- washwashed with sat. aq. NH4Cl (5 mL) and brine
- dry with materialdried over MgSO4
- filtrationfiltered
- customthe solvent was removed under reduced pressure
- customPurification of the residue by FC (3:7 hept-EA)
Sources & evidence
- ORD record
- ord-70ff6aa1909343988ad5211649e69a4c
- Source dataset
- uspto-grants-2014_09
- Patent number
- US08846733B2
Reaction notes
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