ChemicalBook CAS DataBase List (3-PHENYL-5-ISOXAZOLYL)METHANOL

(3-PHENYL-5-ISOXAZOLYL)METHANOL synthesis

6synthesis methods

Product Name:(3-PHENYL-5-ISOXAZOLYL)METHANOL
CAS Number:90924-12-2
Molecular formula:C10H9NO2
Molecular Weight:175.18

107-19-7
5 suppliers
$12.00/25g

932-90-1 Synthesis

932-90-1
127 suppliers
$17.67/1gm:

90924-12-2
86 suppliers
$28.00/100mg

Yield:90924-12-2 76.8%

Reaction Conditions:

Stage #1: Benzaldoximewith N-chloro-succinimide in dichloromethane;Heating;
Stage #2: propargyl alcoholwith triethylamine in dichloromethane;Reflux;

Steps:

2.2 (2) 3-phenyl-5-hydroxymethyl-isoxazole

(2) 3-phenyl-5-hydroxymethyl-isoxazole10.0 mmol of benzaldehyde oxime and30 mL of dry dichloromethane were placed in a 250 mL single-necked roundEP2 752 413 A18510152025303540455055bottom flask. 1.60g (12.0 mmol) of N-chlorosuccinimide (NCS) was added under stirring. After NCS was completelydissolved by slightly heating, 0.56g (10.0 mmol) of 2-propyn-1-ol was added dropwise, and then 20 mL solution of10.1g (10.0 mmol) of triethylamine in dichloromethane. After the addition was complete, the system was refluxed.After the completion of the reaction monitored by TLC, the mother liquor was washed with water, dried over anhydroussodium sulfate, and seperated by column chromatography (Vpetroleum ether: Vethyl acetate = 5:1 - 2:1) to give 3-phenyl-5-hydroxymethyl- isoxazole in 76.8% yield.(3) 3-phenyl-5-aminomethyl-isoxazole

References:

EP2752413,2014,A1 Location in patent:Paragraph 0037