Dimethylformamide → 2,2-Dimethyl-4(tol4-yl)-chrom-3-en-6-al

HRID 1862740Notes

Reaction equation

HRID 1862740 reaction equation
[CH3:1][C:2]1([CH3:20])[CH:11]=[C:10]([C:12]2[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=2)[C:9]2[C:4](=[CH:5][CH:6]=[C:7](Br)[CH:8]=2)[O:3]1.[Li]C(C)(C)C.CN([CH:29]=[O:30])C>C1COCC1.CCCCC.C(OCC)(=O)C>[CH3:1][C:2]1([CH3:20])[CH:11]=[C:10]([C:12]2[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=2)[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([CH:29]=[O:30])[CH:8]=2)[O:3]1

Participants

7

Reactant 3

HCID 6228DimethylformamideHCID 158872872,2-Dimethyl-4(tol-4-yl)-6-bromo-chrom-3-ene2×HCID 178418306HCID 178418306, compound

Product 1

HCID 158872882,2-Dimethyl-4(tol4-yl)-chrom-3-en-6-al

Reagents, catalysts & solvents 3

HCID 8003PentaneSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a cold (−78° C.) solution of 2,2-dimethyl-4(tol-4-yl)-6-bromo-chrom-3-ene (Compound P, 480 mg, 1.45 mmol) in THF (10 mL), was added t-BuLi in pentane (1.7M solution, 1.1 mL) and the mixture was stirred for 30 minutes. DMF (200 mg, 2.9 mmol) was added, the mixture was warmed to ambient temperature and stirred for 3 hours. The reaction was diluted with ethyl acetate (150 mL), washed with brine (10 mL), dried and the solvent was removed by evaporation. Purification by chromatography on silica gel column gave the title compound as a colorless oil.

Workup

  1. stirringstirred for 3 hours
  2. washwashed with brine (10 mL)
  3. customdried
  4. customthe solvent was removed by evaporation
  5. customPurification by chromatography on silica gel column

Sources & evidence

ORD record
ord-fd88bda592b244ba8b27dce229b98566
Source dataset
uspto-grants-2003_03
Patent number
US06538149B1

Reaction notes

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