Water → HCID 19786596, compound

HRID 1646733Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:12]2[C:13](=[O:17])[CH2:14][CH2:15][CH2:16][C:11]=2[O:10][N:9]=1.C([N-]C(C)C)(C)C.[Li+].Cl[C:27]([O:29][CH3:30])=[O:28].O>O1CCCC1.C(OCC)(=O)C>[C:27]([CH:14]1[C:13](=[O:17])[C:12]2[C:8]([C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=3[F:1])=[N:9][O:10][C:11]=2[CH2:16][CH2:15]1)([O:29][CH3:30])=[O:28]

Participants

Conditions

Temperature: -78 °C

Procedure

In a 600 ml anhydrous tetrahydrofuran was dissolved 6,7-dihydro-3-(2-fluorophenyl)-1,2-benzisoxazol-4(5H)-one (20.0 g) under nitrogen. The solution was cooled to -78° C. and 87 ml lithium diisopropylamide was added dropwise. The resulting solution was stirred for ten minutes at -78° C. and 8.7 ml methyl chloroformate was added. Upon warming to room temperature, the reaction mixture was poured into water and ethyl acetate. The layers were separated and the aqueous phase was extracted three times with dichloromethane. The combined organic layers were washed with brine, dried (MgSO4), filtered and concentrated. Column chromatography on silica gel (starting with 10% dichloromethane in hexane and gradually increasing the polarity to 100% DCM) gave 13.5 g of crude product.

Workup

temperatureUpon warming to room temperature
customThe layers were separated
extractionthe aqueous phase was extracted three times with dichloromethane
washThe combined organic layers were washed with brine
dry with materialdried (MgSO4)
filtrationfiltered
concentrationconcentrated
temperaturegradually increasing the polarity to 100% DCM)

Sources & evidence

ORD record: ord-6334df2bc6ae4245874801080c9f65b5
Source dataset: uspto-grants-1993_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05180834

Reaction notes

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