Aluminium lithium hydride → (1-(4-fluorophenyl)-2-((2,3,6-trifluorobenzyl)thio)-1H-imidazol-5-yl)methanol

HRID 2368489Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]([C:13](OCC)=[O:14])=[CH:11][N:10]=[C:9]2[S:18][CH2:19][C:20]2[C:25]([F:26])=[CH:24][CH:23]=[C:22]([F:27])[C:21]=2[F:28])=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1.C(OCC)C.O.[OH-].[Na+].S([O-])([O-])(=O)=O.[Mg+2]>[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]([CH2:13][OH:14])=[CH:11][N:10]=[C:9]2[S:18][CH2:19][C:20]2[C:25]([F:26])=[CH:24][CH:23]=[C:22]([F:27])[C:21]=2[F:28])=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of ethyl 1-(4-fluorophenyl)-2-((2,3,6-trifluorobenzyl)thio)-1H-imidazole-5-carboxylate (10) (1 g, 2.44 mmol) in THF at 0° C. was added lithium aluminum hydride (1M in THF, 4.88 mL, 4.88 mmol). The reaction was stirred for 1 h at 0° C. and at room temperature for 1 h. The solution was diluted with diethyl ether, and water (0.1 mL), 2N NaOH (0.1 mL), water (0.3 mL) and magnesium sulfate were added. The reaction was filtered and washed with THF to obtain (1-(4-fluorophenyl)-2-((2,3,6-trifluorobenzyl)thio)-1H-imidazol-5-yl)methanol (28) as a yellow oil.

Workup

additionwere added
filtrationThe reaction was filtered
washwashed with THF

Sources & evidence

ORD record: ord-000a53afc9ea45feb4fc75480dc59165
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08703776B2

Reaction notes

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