Dimethylformamide → 2,2-Dimethyl-4(5-methyl-thien-2-yl)-chrom-3-en-6-al

HRID 1375275Notes

Reaction equation

HRID 1375275 reaction equation
[CH3:1][C:2]1([CH3:19])[CH:11]=[C:10]([C:12]2[S:13][C:14]([CH3:17])=[CH:15][CH:16]=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:28]=[O:29])C>C1COCC1.CCCCC.C(OCC)(=O)C>[CH3:1][C:2]1([CH3:19])[CH:11]=[C:10]([C:12]2[S:13][C:14]([CH3:17])=[CH:15][CH:16]=2)[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([CH:28]=[O:29])[CH:8]=2)[O:3]1

Participants

7

Reactant 3

HCID 6228DimethylformamideHCID 861915082,2-Dimethyl-4(5-methyl-thien-2-yl)-6-bromo-chrom-3-ene2×HCID 178418306HCID 178418306, compound

Product 1

HCID 1317205762,2-Dimethyl-4(5-methyl-thien-2-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(5-methyl-thien-2-yl)-6-bromo-chrom-3-ene (Compound R, 1.2 g, 3.6 mmol) in THF (10 mL), was added t-BuLi in pentane (1.7M solution, 2.3 mL). After 30 minutes, DMF (465 mg, 5 mmol) was added and the mixture was allowed to warm to ambient temperature and stirred for 3 hours. The mixture 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. washwashed with brine (10 mL)
  2. customdried
  3. customthe solvent was removed by evaporation
  4. customPurification by chromatography on silica gel column

Sources & evidence

ORD record
ord-1e94fa37aba643ae80a803a6cf7c3a7e
Source dataset
uspto-grants-2007_01
Patent number
US07166726B2

Reaction notes

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