1,2,3-Trifluorobenzene → HCID 18985427, compound

HRID 2396657Notes

Reaction equation

HRID 2396657 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]([F:9])[C:7]=1[F:8].[CH3:10][CH2:11][O:12][C:13]([CH:15]1[CH2:21][CH2:20][C:18](=[O:19])[CH2:17][CH2:16]1)=[O:14]>Cl[Ti](OC(C)C)(OC(C)C)OC(C)C>[OH:19][C:18]1([C:4]2[CH:3]=[C:2]([F:1])[C:7]([F:8])=[C:6]([F:9])[CH:5]=2)[CH2:17][CH2:16][CH:15]([C:13]([O:12][CH2:11][CH3:10])=[O:14])[CH2:21][CH2:20]1

Participants

4

Reactant 2

HCID 151471,2,3-TrifluorobenzeneHCID 317638Ethyl 4-oxocyclohexanecarboxylate

Product 1

HCID 18985427HCID 18985427, compound

Reagents, catalysts & solvents 1

HCID 178460663HCID 178460663, compoundCatalyst

Procedure

Thus, 1-triisopropyloxytitanyl, 3,4,5-trifluorobenzene--prepared by transmetalation of 3,4,5-trifluorobenzenemagnesiumbromide using chlorotriisopropyloxytitanium--is reacted chemoselectively with ethyl cyclohexanone-4-carboxylate (1) on the carbonyl group to give ethyl 4-hydroxy-4(3,4,5-trifluorophenyl)cyclohexanecarboxylate. Elimination of water, catalytic hydrogenation over Pd/C, hydrolysis and epimerization using KOH/methanol give the pure trans 4-(3,4,5-trifluorophenyl)cyclohexanecarboxylic acid-(1). The latter is converted into the mixed anhydride using pivaloyl chloride and, using N,O-dimethylhydroxylamine, into the corresponding amide. The latter is reduced in high yield using LiAlH4 to give the aldehyde IIIa'.

Sources & evidence

ORD record
ord-6d3afed531fb47398cb32bd960da4966
Source dataset
uspto-grants-1996_02
Patent number
US05494606

Reaction notes

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