Aluminium lithium hydride → HCID 90418302, compound

HRID 2177191Notes

Reaction equation

[F:1][CH:2]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[C:14]([C:15](OCC)=[O:16])=[C:13]([C:20]([F:23])([F:22])[F:21])[S:12][N:11]=2)=[CH:6][CH:5]=1)[CH3:3].[H-].[H-].[H-].[H-].[Li+].[Al+3]>O1CCCC1>[F:1][CH:2]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[C:14]([CH2:15][OH:16])=[C:13]([C:20]([F:23])([F:22])[F:21])[S:12][N:11]=2)=[CH:6][CH:5]=1)[CH3:3]

Participants

Conditions

Temperature: 0 °C

Procedure

Into a 8-mL vial, was placed ethyl 3-[4-(1-fluoroethyl)phenyl]-5-(trifluoromethyl)-1,2-thiazole-4-carboxylate (290 mg, 0.83 mmol, 1.00 equiv), tetrahydrofuran (1 mL). This was followed by the addition of LiAlH4 (0.83 mL) dropwise with stirring at 0° C. in 1 min. The resulting solution was stirred for 1 h at 0° C. in a water/ice bath. The reaction was then quenched by the addition of 1 mL of water. The resulting solution was extracted with 3×3 mL of ethyl acetate and the organic layers combined and concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1:3). This resulted in 72 mg (28%) of [3-[4-(1-fluoroethyl)phenyl]-5-(trifluoromethyl)-1,2-thiazol-4-yl]methanol as a white solid.

Workup

stirringThe resulting solution was stirred for 1 h at 0° C. in a water/ice bath
customThe reaction was then quenched by the addition of 1 mL of water
extractionThe resulting solution was extracted with 3×3 mL of ethyl acetate
concentrationconcentrated under vacuum
customThis resulted in 72 mg (28%) of [3-[4-(1-fluoroethyl)phenyl]-5-(trifluoromethyl)-1,2-thiazol-4-yl]methanol as a white solid

Sources & evidence

ORD record: ord-537dc42e1ee94189aac192959ce689ca
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09067898B1

Reaction notes

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