Methyl Isocyanate → HCID 59525695, compound

Participants

Reaction Conditions

Reaction Steps

(6-Bromopyridin-2-yl)methanol (1.5 g, 7.98 mmol) and DMAP (0.097 g, 0.798 mmol) were taken up in THF (20 mL) and cooled to 0° C. Methyl isocyanate (0.501 g, 8.78 mmol) was added before warming to room temperature and stirring overnight. The reaction mixture was cooled to 0° C. and sodium hydride (0.319 g, 7.98 mmol) was added. After 30 minutes at 0° C., water was added followed by saturated NH4Cl and the products extracted into EtOAc (2×). The combined organic extracts were washed with brine, dried over MgSO4, filtered, and concentrated in vacuo. Purification of the residue by silica gel chromatography (6-50% EtOAc-hexanes) gave the title compound as a pale yellow solid.

Provenance & Evidence