Trimethylaluminum → HCID 69844669, compound

HRID 1860271Notes

Reaction equation

HRID 1860271 reaction equation
[CH2:1]([O:3][C:4](=[O:19])[CH:5]=[CH:6][C:7]1[S:8][C:9]([NH2:18])=[C:10]([CH2:12][C:13](OCC)=[O:14])[CH:11]=1)[CH3:2].C[Al](C)C>ClCCl>[CH2:1]([O:3][C:4](=[O:19])[CH:5]=[CH:6][C:7]1[S:8][C:9]2[NH:18][C:13](=[O:14])[CH2:12][C:10]=2[CH:11]=1)[CH3:2]

Participants

4

Reactant 2

HCID 16682925TrimethylaluminumHCID 69844816HCID 69844816, compound

Product 1

HCID 69844669HCID 69844669, compoundYield 27.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Ethyl-4-[(ethoxycarbonyl)methyl]-5-amino-2-thiopheneacrylate (150 mg, 0.53 mmol) was dissolved in dichloromethane (20 ml), treated at room temperature with trimethyaluminium (2M in heptane, 1 ml, 2 mmol) and stirred for 1 hour. The reaction was quenched with water, diluted with ethyl acetate, washed with saturated brine solution and dried over magnesium sulfate. The organic phase was evaporated to dryness and the residue chromatographed on silica gel using hexane/ethyl acetate (2:1) as eluent to give 35 mg of 3-(5-oxo-5,6-dihydro-4H-thieno[2,3-b]pyrrol-2-yl)-acrylic acid ethyl ester as a tan colored solid.

Workup

  1. customThe reaction was quenched with water
  2. additiondiluted with ethyl acetate
  3. washwashed with saturated brine solution
  4. dry with materialdried over magnesium sulfate
  5. customThe organic phase was evaporated to dryness
  6. customthe residue chromatographed on silica gel

Sources & evidence

ORD record
ord-72c99d9059e945d1870a12e8d96b38ba
Source dataset
uspto-grants-2003_03
Patent number
US06528653B2

Reaction notes

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