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1,8-Diazabicyclo(5.4.0)undec-7-ene → methyl (E) 3-[2-n-butyl-1-[(2-chlorophenyl)methyl]-1H-imidazol-5-yl]-(2-thienyl)methyl-2-propenoate

HRID 1646117
Notes
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Reaction equation

HRID 1646117 reaction equation
C(O[CH:5]([C:17]1[N:21]([CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[Cl:29])[C:20]([CH2:30][CH2:31][CH2:32][CH3:33])=[N:19][CH:18]=1)[CH:6]([CH2:11][C:12]1[S:13][CH:14]=[CH:15][CH:16]=1)[C:7]([O:9][CH3:10])=[O:8])(=O)C.N12CCCN=C1CCCCC2>C1(C)C=CC=CC=1>[CH2:30]([C:20]1[N:21]([CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[Cl:29])[C:17](/[CH:5]=[C:6](\[CH2:11][C:12]2[S:13][CH:14]=[CH:15][CH:16]=2)/[C:7]([O:9][CH3:10])=[O:8])=[CH:18][N:19]=1)[CH2:31][CH2:32][CH3:33]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 10951051HCID 10951051, compound

Product 1

HCID 11743343methyl (E) 3-[2-n-butyl-1-[(2-chlorophenyl)methyl]-1H-imidazol-5-yl]-(2-thienyl)methyl-2-propenoateYield 76%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of methyl 3-acetoxy-3-[2-n-butyl-1-(2-chlorophenyl)methyl-1H-imidazol-5-yl]-2-[(2-thienyl)methyl]propanoate (4.36 g, 8.92 mmol) in dry toluene (80 mL) was treated with 1,8-diazabicyclo[5,4,0]undec-7-ene (DBU) (3.2 mL, 21.4 mmol), and the resulting solution was heated at 80° C. under argon for 3 hours. The solvent was evaporated, the residue triturated with ether and activated charcoal was added. After filtration, the filtrate was concentrated to 6.29 g of an oil that was chromatographed over silica gel with 65:35 hexane/ethyl acetate to give 2.89 g (76%) of methyl (E)-3-[2-n-butyl-1-[(2-chlorophenyl)methyl]-1H-imidazol-5-yl]-2-(2-thienyl)methyl-2-propenoate whose NMR and TLC (50% ethyl acetate in hexane on silica gel) were identical to the product prepared by Method A.

Workup

  1. customThe solvent was evaporated
  2. customthe residue triturated with ether and activated charcoal
  3. additionwas added
  4. filtrationAfter filtration
  5. concentrationthe filtrate was concentrated to 6.29 g of an oil that
  6. customwas chromatographed over silica gel with 65:35 hexane/ethyl acetate

Sources & evidence

ORD record
ord-087a1d6adac445d080ae0864ef9fdb1b
Source dataset
uspto-grants-1993_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05177096

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes