[OH:1][CH2:2][C:3]1[O:7][N:6]=[C:5]([C:8]([O-:10])=[O:9])[CH:4]=1.[CH3:11][C:12]([Si:15](Cl)([CH3:17])[CH3:16])([CH3:14])[CH3:13].[CH3:19][CH2:20]N(CC)CC>CN(C=O)C.CCOC(C)=O>[CH2:19]([O:9][C:8]([C:5]1[CH:4]=[C:3]([CH2:2][O:1][Si:15]([C:12]([CH3:14])([CH3:13])[CH3:11])([CH3:17])[CH3:16])[O:7][N:6]=1)=[O:10])[CH3:20]To a solution of 5-(hydroxymethyl)isoxazole-3-carboxylate (4.0 g, 23 mmol) and TBSCL (3.7 g, 25 mmol) in DMF is added Et3N (3.4 mL, 24 mmol) dropwise over 20 minutes. The reaction is allowed to stir for 30 minutes after which it is diluted with EtOAc (300 mL), washed with 1 M HCl (3×100 mL), 5% CuSO4 (2×50 mL) and concentrated in vacuo to yield ethyl-5-({[tert-butyl(dimethylsilyl)]oxy}methyl)isoxazole-3-carboxylate as an oily material.
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