Dimethylformamide → HCID 19379061, compound

HRID 2210542Notes

Reaction equation

HRID 2210542 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[C:4]([CH:10]=[C:11]2[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]2)[CH:3]=1.C([Li])CCC.CN(C)[CH:25]=[O:26]>C1COCC1>[C:11]1(=[CH:10][C:4]2[CH:3]=[C:2]([CH:7]=[CH:6][C:5]=2[O:8][CH3:9])[CH:25]=[O:26])[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 19379073HCID 19379073, compoundHCID 178418339Butyllithium

Product 1

HCID 19379061HCID 19379061, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-bromo-2-cycloheptylidenemethylanisole (738 mg, 2.5 mmol) in THF (20 ml) was cooled to -78° C. while stirring under nitrogen. n-Butyllithium (1 ml, 2.5M in Hexane, 2.5 mmol) was added dropwise over 1 minute. N,N-Dimethylformamide (0.5 ml) was added rapidly. The ice bath was removed an the reaction was warmed to room temperature. The reaction was diluted with ethyl acetate (100 ml) and was washed with water (50 ml) and brine (50 ml). The organic solution was dried over MgSO4, filtered and concentrated. The product was purified via flash chromatography to yield 440 mg (1.8 mmol) of the title compound (72%).

Workup

  1. customThe ice bath was removed an the reaction
  2. additionThe reaction was diluted with ethyl acetate (100 ml)
  3. washwas washed with water (50 ml) and brine (50 ml)
  4. dry with materialThe organic solution was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe product was purified via flash chromatography

Sources & evidence

ORD record
ord-a19724ecd8dd475ca9fb6710323fc1e5
Source dataset
uspto-grants-1995_10
Patent number
US05459151

Reaction notes

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