Neopentyl alcohol → HCID 58174094, compound

Participants

Reaction Conditions

Reaction Steps

2-Chloroisonicotinic acid (2.0 g, 13 mmol) was suspended in 50 mL dry CH2Cl2 and treated with oxalyl chloride (3.5 mL, 5.0 g, 39 mmol) plus 3 drops DMF. The mixture was stirred for 4 h, the volatiles removed in vacuo and the residue taken up in 50 mL CH2Cl2. After cooling to 0° C. and treating with neopentyl alcohol (1.7 ml, 1.4 g, 16 mmol), Et3N (2.5 mL, 1.8 g, 18 mmol) was added in portions. The mixture was warmed to 25° C., stirred for 15 h, washed sequentially with 15 mL H2O, 15 mL saturated aqueous NaHCO3, and 15 mL brine, then dried (Na2SO4), filtered, and concentrated in vacuo to give 2.4 g (80%) of 2-chloroisonicotinic acid, 2,2-dimethyl-propyl ester as an oil, used without additional purification: 1H NMR (300 MHz, CDCl3) δ 8.56 (d, J=5.6 Hz, 1H), 7.88 (s, 1H), 7.78 (d J=5.0 Hz, 1H), 4.06 (s, 2H), 1.05 (s, 9H).

Provenance & Evidence