Water → HCID 19786584, compound

HRID 1196580Notes

Reaction equation

[C:1]1([C:7]2[C:11]3[C:12](=[O:16])[CH2:13][CH2:14][CH2:15][C:10]=3[O:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([N-]C(C)C)(C)C.[Li+].[Cl:25][CH2:26][CH2:27][CH2:28]I.O>O1CCCC1.CCOCC>[Cl:25][CH2:26][CH2:27][CH2:28][CH:13]1[C:12](=[O:16])[C:11]2[C:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)=[N:8][O:9][C:10]=2[CH2:15][CH2:14]1

Participants

Conditions

Temperature: -78 °C

Procedure

In 478 ml anhydrous tetrahydrofuran (THF) was dissolved 10.2 g 6,7-dihydro-3-phenyl-1,2-benzisoxazol-4(5H)-one under nitrogen atmosphere with stirring. The solution was cooled to -78° C. and 47.8 ml lithium diisopropylamide (1.5 molar in cyclohexane) was added dropwise. The resulting solution was stirred for 10 minutes at -78° C. and 7.7 ml 1-chloro-3-iodopropane was added. Upon warming to room temperature, the reaction mixture was poured into water and ether. The layers were separated and the aqueous phase was extracted twice with dichloromethane and twice with ether. The combined organic layers were washed with brine and dried (MgSO4). Filtration and concentration gave the crude product. Column chromatography on silica gel (10% ethyl acetate/hexane) gave 6.2 g of 5-(3-chloropropyl)-6,7-dihydro-3-phenyl-1,2-benzisoxazol-4(5H)-one.

Workup

stirringThe resulting solution was stirred for 10 minutes at -78° C.
temperatureUpon warming to room temperature
customThe layers were separated
extractionthe aqueous phase was extracted twice with dichloromethane and twice with ether
washThe combined organic layers were washed with brine
dry with materialdried (MgSO4)
filtrationFiltration and concentration
customgave the crude product

Sources & evidence

ORD record: ord-ae47313d50e841e8ad2f90e25a310e48
Source dataset: uspto-grants-1992_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05114936

Reaction notes

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