Sodium hydride → HCID 44209617, compound

HRID 1033888Notes

Reaction equation

HRID 1033888 reaction equation
C(C1N(C2C(F)=CC=CC=2Cl)C(C=O)=C(C)N=1)CCC.[H-].[Na+].[CH2:23]([C:27]1[N:28]([CH2:45][C:46]2[C:51]([F:52])=[CH:50][CH:49]=[CH:48][C:47]=2[Cl:53])[C:29](/[CH:32]=[C:33](\[CH2:38][C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)/[C:34]([O:36]C)=[O:35])=[CH:30][N:31]=1)[CH2:24][CH2:25][CH3:26].C(C1N(CC2C=CC=CC=2Cl)C(/C(/C)=C/C(O)=O)=CN=1)CCC>C(OCC)(=O)C.CCCCCC.C(COC)OC>[CH2:23]([C:27]1[N:28]([CH2:45][C:46]2[C:51]([F:52])=[CH:50][CH:49]=[CH:48][C:47]=2[Cl:53])[C:29](/[CH:32]=[C:33](\[CH2:38][C:39]2[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=2)/[C:34]([OH:36])=[O:35])=[CH:30][N:31]=1)[CH2:24][CH2:25][CH3:26]

Participants

8

Reactant 4

HCID 24758Sodium hydrideHCID 9974054HCID 9974054, compoundHCID 867465472-n-Butyl-1-(2-chloro-6-fluorophenyl)-methyl-1H-imidazole-5-carboxaldehydeHCID 86747870methyl (E)-[2-n-butyl-1-{(2-chloro-6-fluorophenyl)methyl}-1H-imidazol-5-yl]-2-benzyl-2-propenoate

Product 1

HCID 44209617HCID 44209617, compoundYield 91%

Reagents, catalysts & solvents 3

HCID 8058HexaneSolventHCID 80711,2-DimethoxyethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

The procedure of Example 1(iv-v) was used. From 0.9 g (3.05 mmol) of 2-n-butyl-1-(2-chloro-6-fluorophenyl)-methyl-1H-imidazol-5-carboxaldehyde, 3 g (11 mol) of trimethyl benzylphosphonoacetate, 0.28 g of sodium hydride and glyme (12 mL) held at 60° C. for 1 hour was obtained, after chromatography over silica gel with 50% of hexane in ethyl acetate, 0.44 g (33%) of the trans isomer methyl (E)-[2-n-butyl-1-{(2-chloro-6-fluorophenyl)methyl} -1H-imidazol-5-yl]-2-benzyl-2-propenoate and 0.01 g (8%) of the corresponding cis or (Z)-isomer. The (E)-isomer(0.43 g, 0.98 mmol) was hydrolyzed to the acid and the product was crystallized from methanol to afford 0.38 g (91%) of (E)-3-[2-n-butyl-1-{(2-chloro-6-fluorophenyl)methyl}-1H-imidazol-5-yl]-2-benzyl-2-propenoic acid; mp 204°-206° C.

Workup

  1. customwas obtained
  2. customthe product was crystallized from methanol

Sources & evidence

ORD record
ord-fd874674a31142b5ae74a1e2fa459f67
Source dataset
uspto-grants-1994_05
Patent number
US05312828

Reaction notes

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