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

HRID 1375279Notes

Reaction equation

HRID 1375279 reaction equation
[CH3:1][C:2]1([CH3:19])[CH:11]=[C:10]([C:12]2[S:16][C:15]([CH3:17])=[CH:14][CH:13]=2)[C:9]2[C:4](=[CH:5][CH:6]=[C:7](Br)[CH:8]=2)[S:3]1.[Li]CCCC.CN([CH:28]=[O:29])C>C1COCC1.CCCCCC>[CH3:1][C:2]1([CH3:19])[CH:11]=[C:10]([C:12]2[S:16][C:15]([CH3:17])=[CH:14][CH:13]=2)[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([CH:28]=[O:29])[CH:8]=2)[S:3]1

Participants

6

Reactant 3

HCID 6228DimethylformamideHCID 861914892,2-Dimethyl-4(2-methyl-thien-5-yl)-6-bromo-thiochrom-3-ene2×HCID 178418339Butyllithium

Product 1

HCID 1317205772,2-Dimethyl-4(2-methyl-thien-5-yl)-thiochrom-3-en-6-al

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

To a cold (−78° C.) solution of 2,2-dimethyl-4(2-methyl-thien-5-yl)-6-bromo-thiochrom-3-ene (Compound T, 430 mg, 1.2 mmol) in THF (12 mL) was added n-BuLi in hexane (1.6 M solution, 1 mL). The mixture was gradually warmed to ambient temperature over 1 hour and recooled to −78° C. To this solution was added DMF (220 mg, 3 mmol) and the mixture was stirred at ambient temperature for 16 hours. The reaction was quenched by adding water (10 mL) and ethy lacetate (100 mL). The organic layer was washed with brine (10 mL), dried and the solvent was removed by distillation to obtain the title compound as a pale yellow oil.

Workup

  1. customrecooled to −78° C
  2. customThe reaction was quenched
  3. additionby adding water (10 mL) and ethy lacetate (100 mL)
  4. washThe organic layer was washed with brine (10 mL)
  5. customdried
  6. customthe solvent was removed by distillation

Sources & evidence

ORD record
ord-ecd1cff3ca01489d966f8d529d52db67
Source dataset
uspto-grants-2007_01
Patent number
US07166726B2

Reaction notes

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