Aluminium lithium hydride → HCID 90418686, compound

HRID 2177193Notes

Reaction equation

[F:1][C:2]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[C:15]([C:16](OCC)=[O:17])=[C:14]([C:21]([F:24])([F:23])[F:22])[S:13][N:12]=2)=[CH:7][CH:6]=1)([F:4])[CH3:3].[H-].[H-].[H-].[H-].[Li+].[Al+3]>O1CCCC1>[F:4][C:2]([C:5]1[CH:6]=[CH:7][C:8]([C:11]2[C:15]([CH2:16][OH:17])=[C:14]([C:21]([F:22])([F:23])[F:24])[S:13][N:12]=2)=[CH:9][CH:10]=1)([F:1])[CH3:3]

Participants

Conditions

Temperature: 0 °C

Procedure

Into a 25-mL round-bottom flask, was placed ethyl 3-[4-(1,1-difluoroethyl)phenyl]-5-(trifluoromethyl)-1,2-thiazole-4-carboxylate (450 mg, 1.23 mmol, 1.00 equiv), tetrahydrofuran (4 mL). This was followed by the addition of LiAlH4 (2.5 mL) dropwise with stirring at 0° C. The resulting solution was stirred for 15 min at room temperature (20 degree). The reaction was then quenched by the addition of 5 mL of water. The resulting solution was extracted with 5×5 mL of ethyl acetate and the organic layers combined. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (16:84). This resulted in 110 mg (28%) of [3-[4-(1,1-difluoroethyl)phenyl]-5-(trifluoromethyl)-1,2-thiazol-4-yl]methanol as a yellow solid. Mass spectrum (ESI, m/z): Calcd. for C13H10F5NOS, 324.0 (M+H). found 324.0.

Workup

customInto a 25-mL round-bottom flask, was placed
stirringThe resulting solution was stirred for 15 min at room temperature (20 degree)
customThe reaction was then quenched by the addition of 5 mL of water
extractionThe resulting solution was extracted with 5×5 mL of ethyl acetate
customThis resulted in 110 mg (28%) of [3-[4-(1,1-difluoroethyl)phenyl]-5-(trifluoromethyl)-1,2-thiazol-4-yl]methanol as a yellow solid

Sources & evidence

ORD record: ord-9cb7fb3c94a74fc88127c3d288d73032
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09067898B1

Reaction notes

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