Potassium Sodium Tartrate → 4-(4-Chlorophenyl)-2-(2-methyl-1-imidazolyl)-5-oxazolepropanol

HRID 47930Notes

Reaction equation

HRID 47930 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]([N:19]3[CH:23]=[CH:22][N:21]=[C:20]3[CH3:24])[O:11][C:12]=2[CH2:13][CH2:14][C:15](OC)=[O:16])=[CH:4][CH:3]=1.[H-].COCCO[Al+]OCCOC.[Na+].[H-].[C@H](O)(C([O-])=O)[C@@H](O)C([O-])=O.[Na+].[K+]>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:9]=[C:10]([N:19]3[CH:23]=[CH:22][N:21]=[C:20]3[CH3:24])[O:11][C:12]=2[CH2:13][CH2:14][CH2:15][OH:16])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 9357Potassium Sodium TartrateHCID 21584525Sodium bis(2-methoxyethoxy)aluminiumhydrideHCID 23431804Methyl 4-(4-chlorophenyl)-2-(2-methylimidazol-1-yl)-5-oxazolepropionate

Product 1

HCID 99269974-(4-Chlorophenyl)-2-(2-methyl-1-imidazolyl)-5-oxazolepropanolYield 77.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of methyl 4-(4-chlorophenyl)-2-(2-methylimidazol-1-yl)-5-oxazolepropionate (716.6 g) in toluene (7166 ml) was added dropwise sodium bis(2-methoxyethoxy)aluminum hydride (70% toluene solution, 957.6 g) at not higher than 5° C. over 4 h. To the reaction mixture was added dropwise 10% aqueous Rochelle salt solution (7166 ml) at not higher than 10° C. and the precipitated crystals were collected by filtration. The obtained crystals were washed with 10% Rochelle salt and water, and dried under reduced pressure. The residue was suspended in a mixture of ethyl acetate (717 mL) and isopropyl ether (2866 mL) and the suspension was stirred at room temperature for 3 h. The obtained crystals were collected by filtration to give the title compound (509 g, yield: 77.3%).

Workup

  1. filtrationthe precipitated crystals were collected by filtration
  2. washThe obtained crystals were washed with 10% Rochelle salt and water
  3. customdried under reduced pressure
  4. additionThe residue was suspended in a mixture of ethyl acetate (717 mL) and isopropyl ether (2866 mL)
  5. filtrationThe obtained crystals were collected by filtration

Sources & evidence

ORD record
ord-1fcbb57f5df54e5087957c89615507f6
Source dataset
uspto-grants-2004_03
Patent number
US06699995B1

Reaction notes

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