Ethyl Acetate → HCID 58679082, compound

HRID 1442531Notes

Reaction equation

HRID 1442531 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[C:23]1[NH:27][C:26]2[CH:28]=[C:29]([C:31]([O:33][CH3:34])=[O:32])[S:30][C:25]=2[C:24]=1[CH:35]1[CH2:40][CH2:39][CH2:38][CH2:37][CH2:36]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].Br[CH2:44][CH2:45][O:46][CH2:47][C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1.C(OCC)(=O)C>CN(C)C=O>[CH2:47]([O:46][CH2:45][CH2:44][N:27]1[C:23]([C:10]2[CH:11]=[CH:12][C:13]([O:15][CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[CH:14][C:9]=2[O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[C:24]([CH:35]2[CH2:40][CH2:39][CH2:38][CH2:37][CH2:36]2)[C:25]2[S:30][C:29]([C:31]([O:33][CH3:34])=[O:32])=[CH:28][C:26]1=2)[C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 73833Benzene, ((2-bromoethoxy)methyl)-HCID 58679068HCID 58679068, compound

Product 1

HCID 58679082HCID 58679082, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of methyl 5-(2,4-bisbenzyloxyphenyl)-6-cyclohexyl-4H-thieno[3,2-b]pyrrole-2-carboxylate (1.12 g, 2.03 mmol) in N,N-dimethylformamide (10 ml) was added sodium hydride (60% in oil, 97 mg, 2.43 mmol) under ice-cooling and the mixture was stirred for 10 min. (2-Bromoethoxymethyl)benzene (0.53 ml, 3.24 mmol) was added and the mixture was stirred at room temperature for 4 hr. Ethyl acetate (25 ml) was added to the reaction mixture, and the organic layer was washed successively with water (20 ml×3) and saturated brine (10 ml), and dried over sodium sulfate. After filtration and concentration, the obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=5:1-2:1) to give methyl 4-(2-benzyloxyethyl)-5-(2,4-bisbenzyloxyphenyl)-6-cyclohexyl-4H-thieno[3,2-b]pyrrole-2-carboxylate (1.21 g, yield 87%).

Workup

  1. temperaturecooling
  2. additionwas added
  3. washthe organic layer was washed successively with water (20 ml×3) and saturated brine (10 ml)
  4. dry with materialdried over sodium sulfate
  5. filtrationAfter filtration and concentration
  6. customthe obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=5:1-2:1)

Sources & evidence

ORD record
ord-ce94e13f85dd4a80a150a2dab10a30cf
Source dataset
uspto-grants-2010_02
Patent number
US07659263B2

Reaction notes

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