Nitrogen → 2-(tert-Butyl-dimethyl-silanyloxymethyl)-4-(2-methyl-[1,3]dioxolan-2-yl)-thiazole

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Reaction Conditions

Reaction Steps

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of 1-[2-(tert-butyl-dimethyl-silanyloxymethyl)-thiazol-4-yl]-ethanone (1.77 g, 6.52 mmol) in ethylene glycol (7 mL) was treated with trimethylorthoformate (1.46 mL, 13.29 mmol) followed by LiBF4 (125 mg, 1.30 mmol). The reaction mixture was heated at 95° C. for 4 h. Sat. aq. Na2CO3 (5 mL) was added and the mixture was extracted with Et2O (2×20 mL). The org. extracts were dried over Na2SO4, filtered, and the solvent was removed under reduced pressure. Purification of the residue by FC (20:1 to 3:1 hept-EA) gave the title compound as a brown oil. TLC: rf (1:1 hept-EA)=0.56. LC-MS-conditions 02: tR=1.11 min; [M+H]+=316.36.

Provenance & Evidence