Water → HCID 23114213, compound

HRID 1787176Notes

Reaction equation

HRID 1787176 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:8]2[C:12]3[C:13]([CH3:19])=[CH:14][C:15]([CH3:18])=[C:16]([CH3:17])[C:11]=3[O:10][CH2:9]2)[CH:5]=[CH:6][CH:7]=1.C([Li])CCC.CN([CH:28]=[O:29])C.O>C1COCC1>[CH:28]([C:2]1[CH:3]=[C:4]([C:8]2[C:12]3[C:13]([CH3:19])=[CH:14][C:15]([CH3:18])=[C:16]([CH3:17])[C:11]=3[O:10][CH:9]=2)[CH:5]=[CH:6][CH:7]=1)=[O:29]

Participants

6

Reactant 4

HCID 962WaterHCID 6228DimethylformamideHCID 23113958HCID 23113958, compoundHCID 178418339Butyllithium

Product 1

HCID 23114213HCID 23114213, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-(3-bromophenyl)-4,6,7-trimethyl-2,3-dihydro-1-benzofuran obtained in Reference Example 203 (1.77 g, 5.57 mmol) in THF (20 mL) was added dropwise n-butyllithium (1.6 M hexane solution, 4.18 mL, 6.68 mmol) under argon atmosphere at −78° C., and the mixture was stirred for 30 minutes. To the reaction solution was added dropwise DMF (0.86 mL, 11.14 mmol) at the same temperature, and the mixture was stirred for 30 minutes, and then was warmed to room temperature. Water was added to the reaction solution, which was extracted with ethyl acetate, and then the organic layer was dried over anhydrous sodium sulfate, was filtered, and then was concentrated under reduced pressure to give 1.48 g (yield is quantitative) of the title compound. Oily matter.

Workup

  1. stirringthe mixture was stirred for 30 minutes
  2. extractionwas extracted with ethyl acetate
  3. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  4. filtrationwas filtered
  5. concentrationwas concentrated under reduced pressure
  6. customto give

Sources & evidence

ORD record
ord-a528ad239edd4c00bec1b21972209049
Source dataset
uspto-grants-2009_03
Patent number
US07507841B2

Reaction notes

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