Dimethylformamide → 3-Cyclopentylidenemethyl-4-methoxybenzaldehyde

HRID 2210541Notes

Reaction equation

HRID 2210541 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[C:4]([CH:10]=[C:11]2[CH2:15][CH2:14][CH2:13][CH2:12]2)[CH:3]=1.C([Li])CCC.CN(C)[CH:23]=[O:24]>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:23]=[O:24])[CH2:15][CH2:14][CH2:13][CH2:12]1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 193790694-Bromo-2-cyclopentylidenemethylanisoleHCID 178418339Butyllithium

Product 1

HCID 193790863-Cyclopentylidenemethyl-4-methoxybenzaldehyde

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-bromo-2-cyclopentylidenemethylanisole (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 was dried over MgSO4, filtered and concentrated. The product was purified via flash chromatography. The yield of the title compound (440 mg, 1.8 mmol) was 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 was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe product was purified via flash chromatography

Sources & evidence

ORD record
ord-6eb851a7def3470495181505240d69fb
Source dataset
uspto-grants-1995_10
Patent number
US05459151

Reaction notes

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