Sodium hydride → HCID 14012521, compound

HRID 568697Notes

Reaction equation

[Cl:1][C:2]1[C:10]2[O:9][N:8]=[C:7]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[F:17])[C:6]=2[CH:5]=[CH:4][C:3]=1[OH:18].[H-].[Na+].[CH2:21]([O:23][CH:24]([O:27][CH2:28][CH3:29])[CH2:25]Br)[CH3:22]>CN(C)C=O>[CH2:21]([O:23][CH:24]([O:27][CH2:28][CH3:29])[CH2:25][O:18][C:3]1[CH:4]=[CH:5][C:6]2[C:7]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[F:17])=[N:8][O:9][C:10]=2[C:2]=1[Cl:1])[CH3:22]

Participants

Conditions

Temperature: 80 °C

Procedure

A solution of 5.0 g of 7-chloro-6-hydroxy-3-(2-fluorophenyl)-1,2-benzisoxazole in 30 ml dimethylformamide is added to a suspension of 1 g (50% suspension in oil) sodium hydride in 30 ml of dimethylformamide with stirring. Bromoacetaldehyde diethylacetal (6.2 ml) is added and the reaction mixture is heated at 80° C. for 24 hrs. The resulting dark solution is poured onto ice/water and extracted with four-100 ml portions of ether. The combined ether extracts are washed with dilute sodium hydroxide solution, saturated sodium chloride solution and dried over anhydrous magnesium sulfate. Removal of the solvent followed by recrystallization from ether/petroleum ether affords {[7-chloro-3(2-fluorophenyl)-1,2-benzisoxazol-6-yl]oxy}acetaldehyde diethyl acetal as white needles, mp 59° C.

Workup

additionThe resulting dark solution is poured onto ice/water
extractionextracted with four-100 ml portions of ether
washThe combined ether extracts are washed with dilute sodium hydroxide solution, saturated sodium chloride solution
dry with materialdried over anhydrous magnesium sulfate
customRemoval of the solvent
customfollowed by recrystallization from ether/petroleum ether

Sources & evidence

ORD record: ord-a2962ce59e934351a0ecd5220bc6bd3c
Source dataset: uspto-grants-1988_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04728662

Reaction notes

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