Benzyl Alcohol → HCID 51038392, compound

Participants

Reaction Conditions

Reaction Steps

4-(Pyrimidin-5-yloxy)picolinic acid (1.43 g, 6.58 mmol, 1.00 eq), benzyl alcohol (1.02 mL, 9.88 mmol, 1.50 eq), PS—PPh3 (5.51 g, 14.5 mmol, 2.20 eq) and THF (66 mL) were added to a flame-dried round-bottom flask. The mixture was cooled to 0° C. and diisopropyl azodicarboxylate (2.07 mL, 10.5 mmol, 1.60 eq) was added dropwise. The reaction was allowed to warm to rt and stirred for 1 h. The reaction was filtered and washed with EtOAc. The combined organics were concentrated in vacuo and purified by flash chromatography on silica gel to afford 750 mg (37%) of the title compound as a yellow solid: 1H NMR (400 MHz, CDCl3) δ 9.16 (s, 1H), 8.87 (s, 2H), 8.64 (d, J=5.7 Hz, 1H), 7.66 (d, J=2.5 Hz, 1H), 7.47-7.40 (m, 2H), 7.40-7.38 (m, 1H), 7.38-7.32 (m, 3H), 5.36 (s, 1H); [M+1]+: 308.1.

Provenance & Evidence