Sodium potassium tartrate tetrahydrate → 2-(2-Methyl-1-imidazolyl)-4-(4-trifluoromethylphenyl)-5-oxazolepropanol

HRID 47934Notes

Reaction equation

HRID 47934 reaction equation
[CH3:1][C:2]1[N:3]([C:7]2[O:8][C:9]([CH2:22][CH2:23][C:24](OC)=[O:25])=[C:10]([C:12]3[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][CH:13]=3)[N:11]=2)[CH:4]=[CH:5][N:6]=1.[H-].COCCO[Al+]OCCOC.[Na+].[H-].O.O.O.O.C(C(C(C([O-])=O)O)O)([O-])=O.[Na+].[K+]>C1(C)C=CC=CC=1>[CH3:1][C:2]1[N:3]([C:7]2[O:8][C:9]([CH2:22][CH2:23][CH2:24][OH:25])=[C:10]([C:12]3[CH:13]=[CH:14][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:16][CH:17]=3)[N:11]=2)[CH:4]=[CH:5][N:6]=1

Participants

5

Reactant 3

HCID 2724148Sodium potassium tartrate tetrahydrateHCID 21584525Sodium bis(2-methoxyethoxy)aluminiumhydrideHCID 23431813Methyl 2-(2-methyl-1-imidazolyl)-4-(4-trifluoromethylphenyl)-5-oxazolepropionate

Product 1

HCID 234318072-(2-Methyl-1-imidazolyl)-4-(4-trifluoromethylphenyl)-5-oxazolepropanolYield 81%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent3×

Conditions

Temperature
0 °C

Procedure

Methyl 2-(2-methyl-1-imidazolyl)-4-(4-trifluoromethylphenyl)-5-oxazolepropionate (1.00 g) was dissolved in toluene (15 mL). To the obtained solution was added dropwise a mixture of a 70% solution (1.20 g) of sodium bis(2-methoxyethoxy)aluminum hydride in toluene and toluene (5 mL) at 0° C., and the mixture was stirred at 0° C. for 30 min. To the reaction mixture was carefully added a 10% aqueous solution (50 mL) of potassium sodium (+)-tartrate tetrahydrate, and the mixture was stirred at room temperature for 1 h. The precipitated crystals were collected by filtration, washed successively with a 10% aqueous solution of potassium sodium (+)-tartrate tetrahydrate, pure water and isopropyl ether, and air-dried to give the title compound as crystals (0.75 g, 81%). Recrystallization from ethyl acetate-isopropyl ether gave pale-yellow prism crystals. melting point: 127-129° C.

Workup

  1. additionTo the obtained solution was added dropwise
  2. stirringthe mixture was stirred at room temperature for 1 h
  3. filtrationThe precipitated crystals were collected by filtration
  4. washwashed successively with a 10% aqueous solution of potassium sodium (+)-tartrate tetrahydrate, pure water and isopropyl ether
  5. customair-dried

Sources & evidence

ORD record
ord-57bdc413febb4f2995d8320846b37e86
Source dataset
uspto-grants-2004_03
Patent number
US06699995B1

Reaction notes

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