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

HRID 1198320Notes

Reaction equation

HRID 1198320 reaction equation
C(N1[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1)=O.[F:9][C:10]1[C:15]([F:16])=[CH:14][CH:13]=[CH:12][C:11]=1[Li].[CH:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C([Li])CCC.[O:29]1CCC[CH2:30]1>O1CCCC1.CN(C)CCN(C)C>[CH2:4]([CH:18]1[CH2:23][CH2:22][C:21]([C:14]2[CH:13]=[CH:12][C:11]([CH:30]=[O:29])=[C:10]([F:9])[C:15]=2[F:16])=[CH:20][CH2:19]1)[CH2:5][CH2:6][CH2:7][CH3:8]

Participants

7

Reactant 5

HCID 241BenzeneHCID 8028TetrahydrofuranHCID 174291-PiperidinecarboxaldehydeHCID 178418339ButyllithiumHCID 178506716HCID 178506716, compound

Product 1

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

Reagents, catalysts & solvents 1

HCID 86588997Thf tmedaSolvent

Conditions

Temperature
-20 °C

Procedure

0.12 mol of N-formylpiperidine in 20 ml of tetrahydrofuran is added to 0.1 mol of 4-(4-pentycyclohex-1-enyl)- 2,3-difluorophenyllithium (prepared from the benzene with n-butyllithium in tetrahydrofuran/tetramethylethylenediamine analogously to Example 7a)) at -70° C. and the mixture is warmed to -20° C. in the course of 1 hour. Acidification and customary working up give the aldehyde.

Sources & evidence

ORD record
ord-39b4a4d3109b4dc59bc40f943feea4a6
Source dataset
uspto-grants-1994_01
Patent number
US05279764

Reaction notes

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