ChemicalBook CAS DataBase List Isoxazole, 5-(chloromethyl)-3-(1-methylethyl)- (9CI)

Isoxazole, 5-(chloromethyl)-3-(1-methylethyl)- (9CI) synthesis

4synthesis methods

Product Name:Isoxazole, 5-(chloromethyl)-3-(1-methylethyl)- (9CI)
CAS Number:64988-71-2
Molecular formula:C7H10ClNO
Molecular Weight:159.61

14633-17-1
23 suppliers
$65.00/100mg

Isoxazole, 5-(chloromethyl)-3-(1-methylethyl)- (9CI)

64988-71-2
23 suppliers
$58.00/100mg

Yield:64988-71-2 43%

Reaction Conditions:

with methanesulfonyl chloride;triethylamine in dichloromethane at 0 - 25; for 2 h;

Steps:

15.2 5-(Chloromethyl)-3-isopropylisoxazole

3-isopropylisoxazol-5-yl) methanol (150 mg, 1.06 mmol) and triethylamine (322 mg, 3.16 mmol) were dissolved in anhydrous dichloromethane (5 mL).
Methanesulfonyl chloride (237 mg, 2.12 mmol) was added at 0°C.
The reaction solution was slowly warmed to 25°C and stirred for 2 hours.
The reaction was quenched by the addition of saturated sodium bicarbonate aqueous solution (10 mL) and extracted with dichloromethane (10 mL x 3).
The organic phases were combined, washed with saturated sodium chloride aqueous solution (30 mL), dried over anhydrous sodium sulfate, and concentrated under reduced pressure to give 5-(chloromethyl)-3-isopropylisoxazole (72.5 mg, as a yellow oil) with a yield of 43%.
¹H NMR: (400 MHz, Methanol-d₄) δ 6.44(s, 1H), 4.74(s, 2H), 3.27-3.25(m, 1H), 1.35(d, J = 3.4 Hz, 6H).

References:

EP3299371,2018,A1 Location in patent:Paragraph 0151; 0155; 0156