Methyl 4-(3,4-dichlorophenyl)-2-(2-methyl-1-imidazolyl)-5-oxazolepropionate → 4-(3,4-Dichlorophenyl)-2-(2-methyl-1-imidazolyl)-5-oxazolepropanol

HRID 747443Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[N:10]=[C:11]([N:20]3[CH:24]=[CH:23][N:22]=[C:21]3[CH3:25])[O:12][C:13]=2[CH2:14][CH2:15][C:16](OC)=[O:17])[CH:5]=[CH:6][C:7]=1[Cl:8].O.C(C(C(C([O-])=O)O)O)([O-])=O.[K+].[Na+].O.O.[Na+].[K+].C(C(C(C([O-])=O)O)O)([O-])=O>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[N:10]=[C:11]([N:20]3[CH:24]=[CH:23][N:22]=[C:21]3[CH3:25])[O:12][C:13]=2[CH2:14][CH2:15][CH2:16][OH:17])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

Conditions

Temperature: 0 °C

Procedure

Methyl 4-(3,4-dichlorophenyl)-2-(2-methyl-1-imidazolyl)-5-oxazolepropionate (0.67 g) was dissolved in toluene (5 ml). To the obtained solution was added dropwise a mixture of a 70% toluene solution (0.81 g) of sodium dihydrobis(2-methoxyethoxy)aluminate, and toluene (5 ml) at 0° C., which was stirred at 0° C. for 1 hour. To the reaction mixture was carefully added a 10% aqueous solution of (+)-sodium potassium tartrate sesquihydrate (50 ml), which was stirred at room temperature for 1 hour. The precipitated crystals were filtered, washed in sequence with a 10% aqueous solution of (+)-sodium potassium tartrate sesquihydrate, pure water, and isopropyl ether, and air-dried to give crystals of 4-(3,4-dichlorophenyl)-2-(2-methyl-1-imidazolyl)-5-oxazolepropanol (0.46 g, 74%). Recrystallization from acetone-hexane gave pale yellow prisms. Melting point 140-141° C.

Workup

additionTo the obtained solution was added dropwise
stirringwas stirred at room temperature for 1 hour
filtrationThe precipitated crystals were filtered
washwashed in sequence with a 10% aqueous solution of (+)-sodium potassium tartrate sesquihydrate, pure water, and isopropyl ether
customair-dried

Sources & evidence

ORD record: ord-12ab730f618e4e3ca20e5439fd8e4e28
Source dataset: uspto-grants-2008_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07396848B1

Reaction notes

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