Ethyl Acetate → HCID 58679114, compound

HRID 1442529Notes

Reaction equation

HRID 1442529 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[CH:24]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].Br[CH:38]1[CH2:43][CH2:42][CH2:41][CH:40]=[CH:39]1.C(OCC)(=O)C>CN(C)C=O>[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:43]1[CH2:42][CH2:41][CH2:40][CH:39]=[CH:38]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 1370573-BromocyclohexeneHCID 58679085HCID 58679085, compound

Product 1

HCID 58679114HCID 58679114, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of methyl 5-(2,4-bisbenzyloxyphenyl)-4H-thieno[3,2-b]pyrrole-2-carboxylate (1.36 g, 2.90 mmol) in N,N-dimethylformamide (15 ml) was added sodium hydride (60% in oil, 127 mg, 3.19 mmol) under ice-cooling and the mixture was stirred for 20 min. 3-Bromocyclohexene (0.34 ml, 2.95 mmol) was added and the mixture was stirred under ice-cooling for 50 min. Ethyl acetate (20 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, a mixed solvent (10 ml) of hexane:ethyl acetate (10:1) was added. The precipitated solid was collected by filtration. The solid was washed with a mixed solvent (5 ml×3) of hexane:ethyl acetate (10:1), and dried under reduced pressure to give methyl 5-(2,4-bisbenzyloxyphenyl)-6-(cyclohex-2-enyl)-4H-thieno[3,2-b]pyrrole-2-carboxylate (1.35 g, yield 85%).

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred under ice-
  3. temperaturecooling for 50 min
  4. washthe organic layer was washed successively with water (20 ml×3) and saturated brine (10 ml)
  5. dry with materialdried over sodium sulfate
  6. filtrationAfter filtration and concentration
  7. additiona mixed solvent (10 ml) of hexane:ethyl acetate (10:1) was added
  8. filtrationThe precipitated solid was collected by filtration
  9. washThe solid was washed with a mixed solvent (5 ml×3) of hexane:ethyl acetate (10:1)
  10. customdried under reduced pressure

Sources & evidence

ORD record
ord-2b01da915ff24b749cf9d2f1431930ef
Source dataset
uspto-grants-2010_02
Patent number
US07659263B2

Reaction notes

Loading…