Hydrochloric Acid → HCID 15124000, compound

HRID 1084854Notes

Reaction equation

HRID 1084854 reaction equation
[CH3:1][C:2]1[C:6]2[C:7]([O:11][CH3:12])=[CH:8][CH:9]=[CH:10][C:5]=2[O:4][C:3]=1[C:13]([O:15][CH2:16][CH3:17])=[O:14].[S:18]1[CH:22]=[CH:21][CH:20]=[C:19]1[C:23](Cl)=[O:24].[Cl-].[Al+3].[Cl-].[Cl-].Cl>ClCCCl>[CH3:1][C:2]1[C:6]2[C:7]([O:11][CH3:12])=[CH:8][CH:9]=[C:10]([C:23]([C:19]3[S:18][CH:22]=[CH:21][CH:20]=3)=[O:24])[C:5]=2[O:4][C:3]=1[C:13]([O:15][CH2:16][CH3:17])=[O:14]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 789282-Thiophenecarbonyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 9497663Ethyl 4-methoxy-3-methyl-2-benzofurancarboxylate

Product 1

HCID 15124000HCID 15124000, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent2×

Procedure

To a solution of ethyl 3-methyl-4-methoxy-benzofuran-2-carboxylate (3.48 g, 14.86 mmol) in dry 1,2-dichloroethane (15 mL) was added a solution of thiophene-2-carbonyl chloride (6.54 g, 44.61 mmol) in 1,2-dichloroethane (10 mL) followed by the portionwise addition of aluminum chloride (7.92 g, 59.40 mmol). An exothermic reaction ensued and the mixture was allowed to stir until gas evolution had slowed, then warmed to reflux for 2 hours. Upon cooling the reaction mixture was poured into 2N HCl (100 mL) and extracted with methylene chloride (4×25 mL). The combined organic extracts were washed with 5% NaHCO3, dried (Na2SO4), and concentrated to a brown solid (5.40 g). Recrystallization from ethanol/benzene afforded pure ethyl 3-methyl-4-methoxy-7-(2-thienoyl)benzofuran-2-carboxylate, compound 1. mp 179°-182° C.; 1H NMR d 1.40 (3H, t, J=6 Hz), 2.77 (3H, s), 4.04 (3H, s), 4.42 (2H, q, J=6 Hz), 6.75 (1H, d, J=8 Hz), 7.17 (1H, dd, J=4 Hz), 7.72 (2H, m), 7.86 (1H, d, J=8 Hz).

Workup

  1. customAn exothermic reaction
  2. temperaturewarmed
  3. temperatureto reflux for 2 hours
  4. temperatureUpon cooling the reaction mixture
  5. extractionextracted with methylene chloride (4×25 mL)
  6. washThe combined organic extracts were washed with 5% NaHCO3
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated to a brown solid (5.40 g)
  9. customRecrystallization from ethanol/benzene afforded pure ethyl 3-methyl-4-methoxy-7-(2-thienoyl)benzofuran-2-carboxylate, compound 1

Sources & evidence

ORD record
ord-3d75110fd5744553be1e16679baa66ce
Source dataset
uspto-grants-1991_04
Patent number
US05006549

Reaction notes

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