Sodium hydride → HCID 11356093, compound

Participants

Reaction Steps

To a solution of 0.5 g (4.31 mmol) of [1-(hydroxymethyl)cyclobutyl]methanol in 15 mL of N,N-dimethylformamide:tetrahydrofuran (1:1), was added a 60% dispersion of 0.165 g (4.31 mmol) sodium hydride in oil. After stirring for 15 min, 0.71 g (4.31 mmol) of 2-bromothiazole was added and the contents refluxed for 3 h. A saturated solution of sodium bicarbonate was added followed by ethyl acetate. The organic phase was isolated, dried with magnesium sulfate and concentrated under vacuum. The crude product was purified by silica gel chromatography eluting with ethyl acetate:hexane (4:6) to afford 0.340 g (40%) of {1-[(1,3-thiazol-2-yloxy)methyl]cyclobutyl}methanol as a colorless oil. 1H NMR (300 MHz, CDCl3) δ 7.05 (d, J=4 Hz, 1H), 6.64 (d, J=4 Hz, 1H), 4.51 (s, 2H), 3.59 (s, 2H), 2.03-1.72 (m, 6H). GC-MS m/z 200 (M+H).

Provenance & Evidence