Triethylamine → ethyl (E)-3-[2-n-butyl-1-{(2-chlorophenyl)methyl)-1H-imidazol-5-yl]-2-(5-methyl-2-furyl)methyl-2-propenyl carbonate

HRID 1646126Notes

Reaction equation

HRID 1646126 reaction equation
[CH2:1]([C:5]1[N:6]([CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[Cl:28])[C:7](/[CH:10]=[C:11](\[CH2:14][C:15]2[O:16][C:17]([CH3:20])=[CH:18][CH:19]=2)/[CH2:12][OH:13])=[CH:8][N:9]=1)[CH2:2][CH2:3][CH3:4].C(N(CC)CC)C.Cl[C:37]([O:39][CH2:40][CH3:41])=[O:38].C(OCC)(=O)C>C(Cl)Cl>[C:37](=[O:38])([O:13][CH2:12]/[C:11](/[CH2:14][C:15]1[O:16][C:17]([CH3:20])=[CH:18][CH:19]=1)=[CH:10]/[C:7]1[N:6]([CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[Cl:28])[C:5]([CH2:1][CH2:2][CH2:3][CH3:4])=[N:9][CH:8]=1)[O:39][CH2:40][CH3:41]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 10928Ethyl chloroformateHCID 70044288HCID 70044288, compound

Product 1

HCID 86746471ethyl (E)-3-[2-n-butyl-1-{(2-chlorophenyl)methyl)-1H-imidazol-5-yl]-2-(5-methyl-2-furyl)methyl-2-propenyl carbonate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (E)-3-[2-n-butyl-1-{(2-chlorophenyl)methyl}-1H-imidazol-5-yl]-2-(5-methyl-2-furyl)methyl-2-propenol (6.86 mmol) in methylene chloride (20 mL) and triethylamine (12.4 mmol) cooled to 0° C. under argon is added dropwise ethyl chloroformate (1.34 g, 1.18 ml, 12 mmol). The reaction is then stirred at ambient temperature overnight. Ethyl acetate is added, the precipitate filtered and the concentrated filtrate is flash chromatographed over silica gel with 3:7 hexane/ethyl acetate to provide the title compound.

Workup

  1. filtrationthe precipitate filtered
  2. customchromatographed over silica gel with 3:7 hexane/ethyl acetate

Sources & evidence

ORD record
ord-c23d725c917d4d2781f09f5608db8333
Source dataset
uspto-grants-1993_01
Patent number
US05177096

Reaction notes

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