Water → HCID 53770206, compound

HRID 1646734Notes

Reaction equation

HRID 1646734 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+].Br[CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28].O>O1CCCC1.CCOCC>[CH2:30]([O:29][C:27](=[O:28])[CH2:26][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)[CH3:31]

Participants

7

Reactant 4

HCID 962WaterHCID 7748Ethyl bromoacetateHCID 2724682Lithium diisopropylamideHCID 12344070HCID 12344070, compound

Product 1

HCID 53770206HCID 53770206, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

In 115 ml anhydrous tetrahydrofuran was dissolved 2.44 g of 6,7-dihydro-3-phenyl-1,2-benzisoxazol-4(5H)-one under nitrogen. The solution was cooled to -78° C. and 11.5 ml lithium diisopropylamide was added dropwise. The resultant solution was stirred for 15 minutes at -78° C. and ethyl bromoacetate (2.6 ml) 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 three times with dichloromethane and once with ether. The combined organic layers were washed with brine and dried (MgSO4). Flash column chromatography (30% ethyl acetate/hexane) gave 2.94 g of 4,5,6,7-tetrahydro-4-oxo-3-phenyl-1,2-benzisoxazol-5-acetic acid ethyl ester

Workup

  1. temperatureUpon warming to room temperature
  2. customThe layers were separated
  3. extractionthe aqueous phase was extracted three times with dichloromethane
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried (MgSO4)

Sources & evidence

ORD record
ord-8fc83c010e974f12a3c6691aef8c7a7b
Source dataset
uspto-grants-1993_01
Patent number
US05180834

Reaction notes

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