Water → 4-Methoxy-2-methoxycarbonyl-3-(2-phenylethyl)benzo[b]thiophene

HRID 230882Notes

Reaction equation

HRID 230882 reaction equation
[SH:1][C:2]1[CH:17]=[CH:16][CH:15]=[C:14]([O:18][CH3:19])[C:3]=1[C:4](=O)[CH:5]=[CH:6][CH:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH2:8]1.C(N(CC)CC)C.Br[CH2:28][C:29]([O:31][CH3:32])=[O:30].O>ClCCl>[CH3:19][O:18][C:14]1[C:3]2[C:4]([CH2:5][CH2:6][C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=3)=[C:28]([C:29]([O:31][CH3:32])=[O:30])[S:1][C:2]=2[CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 60984Methyl bromoacetateHCID 671358342'-Mercapto-6'-methoxydihydrochalcone

Product 1

HCID 231035484-Methoxy-2-methoxycarbonyl-3-(2-phenylethyl)benzo[b]thiophene

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2′-mercapto-6′-methoxydihydrochalcone (1.2 g) and triethylamine (0.92 mL) in dichloromethane (10 mL) was added methyl bromoacetate (0.46 mL), and the mixture was stirred at room temperature for 3 hours. The reaction mixture was poured into water, and the resulting mixture was extracted with diethyl ether. The extract was washed with water and brine, and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and the residue was dissolved in methanol (15 mL). To the solution was added sodium methoxide (28% methanol solution, 1.7 mL), and the mixture was stirred at room temperature overnight. The crystals precipitated from the reaction mixture were collected by filtration and dried under reduced pressure to give the title compound (1.09 g).

Workup

  1. extractionthe resulting mixture was extracted with diethyl ether
  2. washThe extract was washed with water and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was removed under reduced pressure
  5. dissolutionthe residue was dissolved in methanol (15 mL)
  6. additionTo the solution was added sodium methoxide (28% methanol solution, 1.7 mL)
  7. stirringthe mixture was stirred at room temperature overnight
  8. customThe crystals precipitated from the reaction mixture
  9. filtrationwere collected by filtration
  10. customdried under reduced pressure

Sources & evidence

ORD record
ord-201aafc2a161429aa9fc849cac73612d
Source dataset
uspto-grants-2009_07
Patent number
US07566699B2

Reaction notes

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