Ethyl Acetate → HCID 58679085, compound

HRID 1442528Notes

Reaction equation

HRID 1442528 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:12]=[CH:11][C:10]=1/[CH:23]=[CH:24]/[C:25]1[S:29][C:28]([C:30]([O:32][CH3:33])=[O:31])=[CH:27][C:26]=1[N+:34]([O-])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.P(OCC)(OCC)OCC.C(OCC)(=O)C>C1(C)C=C(C)C=C(C)C=1>[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:12]=[CH:11][C:10]=1[C:23]1[NH:34][C:26]2[CH:27]=[C:28]([C:30]([O:32][CH3:33])=[O:31])[S:29][C:25]=2[CH:24]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 31215Triethyl phosphiteHCID 58679079HCID 58679079, compound

Product 1

HCID 58679085HCID 58679085, compoundYield 47.2%

Reagents, catalysts & solvents 1

HCID 7947MesityleneSolvent

Conditions

Temperature
160 °C

Procedure

To a solution of methyl (E)-5-[2-(2,4-bisbenzyloxyphenyl)vinyl]-4-nitrothiophene-2-carboxylate (3.08 g, 6.13 mmol) in mesitylene (15 ml) was added triethyl phosphite (3.15 ml, 18.4 mmol), and the mixture was stirred at 160° C. for 43 hr. The reaction mixture was allowed to cool to room temperature, and ethyl acetate (50 ml) was added. The organic layer was washed successively with 1N hydrochloric acid (30 ml), water (30 ml×2) and saturated brine (20 ml), and dried over sodium sulfate. After filtration and concentration, isopropyl alcohol (20 ml) was added to the obtained residue and the precipitated solid was collected by filtration. The solid was washed with isopropyl alcohol (10 ml×3) to give methyl 5-(2,4-bisbenzyloxyphenyl)-4H-thieno[3,2-b]pyrrole-2-carboxylate (1.36 g, yield 47%).

Workup

  1. temperatureto cool to room temperature
  2. washThe organic layer was washed successively with 1N hydrochloric acid (30 ml), water (30 ml×2) and saturated brine (20 ml)
  3. dry with materialdried over sodium sulfate
  4. filtrationAfter filtration and concentration, isopropyl alcohol (20 ml)
  5. additionwas added to the obtained residue
  6. filtrationthe precipitated solid was collected by filtration
  7. washThe solid was washed with isopropyl alcohol (10 ml×3)

Sources & evidence

ORD record
ord-5f7438850e1b49bd8a4e2cea71d7e3cd
Source dataset
uspto-grants-2010_02
Patent number
US07659263B2

Reaction notes

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