Triethylamine → HCID 20093450, compound

Participants

Reaction Steps

A stirred solution under nitrogen of 5-amino-1,3-dimethylpyrazole (7.09 g, 63.8 mmol) and triethylamine (10 mL) in sieve-dried methylene chloride (100 mL) was chilled in an ice-bath and n-butyryl chloride (7.3 mL, 70.3 mmol) was added dropwise. After 1 hour, the reaction mixture was shaken with 50 mL of 1M K2HPO4 solution and the aqueous phase was further extracted with CH2Cl2 (2×70 mL). The organic phase was dried over MgSO4, filtered and then evaporated to dryness to give 13.2 g of an orange-yellow oil. This was purified by chromatography on SiO2 (300 g), developing with EtOAc/hexane (45:55) to give the Step A compound (10.53 g; 91%) as an oil. 1H NMR (200 MHz, CDCl3), δ 6.00 (s, 1H), 3.65 (s, 3H), 2.37 (t, 2H, J=9 Hz), 2.22 (s, 3H), 1.62-1.90 (m, 2H), 1.01 (t, 3H, J=9 Hz).

Provenance & Evidence