Diethyl Ether → HCID 86751272, compound
Reaction equation
Br[C:2]1[S:6][CH:5]=[N:4][CH:3]=1.C([Li])CCC.[F:12][C:13]([F:23])([F:22])[C:14]1[CH:21]=[CH:20][CH:19]=[CH:18][C:15]=1[CH:16]=O.CC[O:26]CC>>[OH:26][C:15]1([CH:18]=[CH:19][CH:20]=[CH:21][CH:14]1[C:13]([F:23])([F:22])[F:12])[CH2:16][C:2]1[S:6][CH:5]=[N:4][CH:3]=1Participants
Conditions
- Temperature
- -78 °C
Procedure
To a solution of 5-bromothiazole in 12 ml of ether at -78° C., 2.1 ml of 2.5M n-butyl lithium were added dropwise over 30 minutes. The resulting brown suspension was stirred at -78° C. for 2 hours and then a solution of 2-(trifluoromethyl)benzaldehyde in 2 ml of diethyl ether was added dropwise. The reaction was quenched 1 hour later with 10 ml of water saturated with ammonium chloride. The reaction mixture was extracted twice with 2 ml of diethyl ether. The organic phases were combined, dried (MgSO4) and concentrated in vacuo to yield 1.16 g of a brown oil. This oil was heated to 50° C. at 0.01 mm Hg to remove volatiles leaving 1.16 g of brown oil which was then chromatographed on silica gel using hexane-ethyl acetate (75-25) as the eluant. The last fraction to come off the column contained 297 mg of the desired product, 5-(1-hydroxy-2'-trifluoromethylbenzyl)-thiazole.
Workup
- customThe reaction was quenched 1 hour later with 10 ml of water saturated with ammonium chloride
- extractionThe reaction mixture was extracted twice with 2 ml of diethyl ether
- dry with materialdried (MgSO4)
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-b6e98c61486a43d4b29c814692c5d692
- Source dataset
- uspto-grants-1997_09
- Patent number
- US05672567
Reaction notes
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