Potassium Hydroxide → HCID 23117152, compound

HRID 1921266Notes

Reaction equation

Cl.[NH2:2][OH:3].[CH:4]1([C:10]([C:12]2[CH:17]=[CH:16][C:15]([O:18][CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[CH:14][C:13]=2F)=O)[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5]1.[OH-].[Na+].[OH-].[K+]>O.CCO>[CH2:19]([O:18][C:15]1[CH:16]=[CH:17][C:12]2[C:10]([CH:4]3[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5]3)=[N:2][O:3][C:13]=2[CH:14]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

Conditions

Temperature: 6 °C

Procedure

A solution of hydroxylamine hydrochloride (11.7 g) in warm water (100 ml) was poured into a mixture of cyclohexyl (4-benzyloxy-2-fluorophenyl)methanone (20.22 g, 64.7 mmol) and EtOH (54 ml). A solution of sodium hydroxide (11.13 g, 0.278 mol) in water (54 ml) was then added as rapidly as the reflux permitted. The reaction mixture was heated for 12 h and then most of the EtOH was removed by distillation. To the residue was added a solution of potassium hydroxide (8.7 g, 0.155 mol) in water (54 ml). The mixture was refluxed for 2 days, then cooled to about 6° C. and stirred vigorously. A white solid was obtained, which was thoroughly washed with water and triturated with diisopropyl ether. The benzisoxazole was obtained as a white powder (12.26 g, 62%) after filtration. mp 110° C.

Workup

temperatureThe reaction mixture was heated for 12 h
custommost of the EtOH was removed by distillation
temperatureThe mixture was refluxed for 2 days
customA white solid was obtained
washwhich was thoroughly washed with water
customtriturated with diisopropyl ether

Sources & evidence

ORD record: ord-0c7a9d726769428bb7f6185f5ee96396
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08173679B2

Reaction notes

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