application of (trimethylisoxazol-5-yl)methanol_industrial additives

background and overview^[1]

(trimethylisoxazol-5-yl)methanol is an alcohol derivative that can be used as a pharmaceutical synthesis intermediate.

structure

preparation^[1]

1) add ncs (2.7g, 20mmol) to a solution of acetaldoxime (1g, 16.9mmol) in anhydrous thf (15ml) at room temperature. after stirring for 2 hours, a dilute solution of propargyl alcohol (1.42 g, 25 mmol) in anhydrous thf (4 ml) was slowly added, and after 30 minutes, a dilute solution of tea (2.78 ml, 20 mmol) in anhydrous thf was added. then add continuously. after 1 hour with vigorous stirring, water (10 ml) was added to the reaction mixture. the suspension was extracted with ea (20 ml × 3), the organic layer was dried over mgso4, filtered, and concentrated in vacuo. the residue was purified by silica gel flash column chromatography (ea/hex 1:1) to give (3-methylisoxazol-5-yl)methanol.

(0.93g, 8.28mmol, 49%). 1hnmr (300mhz, cdcl3) δ6.09 (s, 1h), 4.73 (s, 2h), 2.52 (br, 1h), 2.34 (s, 3h). 13cnmr (75mhz, cdcl3) δ171.09, 159.85, 102.53, 56.46, 11.37.

apply^[1]

(trimethylisoxazol-5-yl)methanol, for example, prepare the following compound:

(trimethylisoxazol-5-yl)methanol (0.5g, 4.42) was added to acetone (19ml) at 0°c and jones reagent (2.21ml) was added, and the mixture was stirred for 3 hours. the reaction was monitored by tlc and after the reaction was terminated, the mixture was adjusted to ph 2 with 1 n hcl solution. the residue was extracted with ea (20 ml×3), and the combined organic layers were dried over mgso4, filtered, and concentrated in vacuo. the residue was purified by silica gel flash column chromatography (ea/hex 1:1) to give the desired product (0.63 g, 4.97 mmol, 100%). 1hnmr (300mhz, ch3od) δ6.90 (s, 1h), 2.35 (s, 3h). 13cnmr (75mhz, ch3od) δ161.05, 160.82, 158.16, 109.46, 98.81.