Benzene → 4-(4-Pentylcyclohex-1-enyl)-2,3-difluorobenzaldehyde

HRID 248771Notes

Reaction equation

HRID 248771 reaction equation
[CH:1](N1CCCCC1)=[O:2].[CH2:9]([CH:14]1[CH2:19][CH2:18][C:17]([C:20]2[CH:25]=[CH:24][C:23]([Li])=[C:22]([F:27])[C:21]=2[F:28])=[CH:16][CH2:15]1)[CH2:10][CH2:11][CH2:12][CH3:13].C1C=CC=CC=1.C([Li])CCC>O1CCCC1.O1CCCC1.CN(C)CCN(C)C>[CH2:9]([CH:14]1[CH2:19][CH2:18][C:17]([C:20]2[CH:25]=[CH:24][C:23]([CH:1]=[O:2])=[C:22]([F:27])[C:21]=2[F:28])=[CH:16][CH2:15]1)[CH2:10][CH2:11][CH2:12][CH3:13]

Participants

7

Reactant 4

HCID 241BenzeneHCID 174291-PiperidinecarboxaldehydeHCID 178418339ButyllithiumHCID 178506671HCID 178506671, compound

Product 1

HCID 145484864-(4-Pentylcyclohex-1-enyl)-2,3-difluorobenzaldehyde

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 86588997Thf tmedaSolvent

Conditions

Temperature
-20 °C

Procedure

0.12 mol of N-formylpiperidine in 20 ml of tetrahydrofuran is added at -70° C. to 0.1 mol of 4-(4-pentylcyclohex-1-enyl)-2,3-difluorophenyllithium (prepared from the benzene with n-butyllithium in tetrahydrofuran/tetramethylethylenediamine analogously to Example 1a)) and the mixture is warmed to -20° C. during the course of 1 hour. Acidifying and customary working up gives the aldehyde.

Sources & evidence

ORD record
ord-795b5b9ab053432fbae958db29569890
Source dataset
uspto-grants-1993_05
Patent number
US05211878

Reaction notes

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