Hydrochloric Acid → HCID 22667439, compound

HRID 1007053Notes

Reaction equation

HRID 1007053 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:10]2[CH:15]=[CH:14][C:13]([CH:16]3[CH2:21][CH2:20][CH:19]([CH2:22][CH2:23][CH3:24])[CH2:18][CH2:17]3)=[CH:12][CH:11]=2)[CH:5]=[C:6]([F:9])[C:7]=1[F:8].C([Li])CCC.CN(C)[CH:32]=[O:33].Cl>O1CCCC1>[F:1][C:2]1[C:7]([F:8])=[C:6]([F:9])[CH:5]=[C:4]([C:10]2[CH:15]=[CH:14][C:13]([CH:16]3[CH2:21][CH2:20][CH:19]([CH2:22][CH2:23][CH3:24])[CH2:18][CH2:17]3)=[CH:12][CH:11]=2)[C:3]=1[CH:32]=[O:33]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 150149211,1′-Biphenyl, 3,4,5-trifluoro-4′-(4-propylcyclohexyl)-HCID 178418339Butyllithium

Product 1

HCID 22667439HCID 22667439, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 46 mmol of 3,4,5-trifluoro-4′-(4-propylcyclohexyl)biphenyl in 100 ml of dry tetrahydrofuran is cooled to −75° C., and 50 mmol of n-butyllithium (1.6 M solution in n-hexane) are added dropwise under a protective-gas atmosphere at such a rate that the internal temperature does not exceed −75° C. The mixture is subsequently stirred at this temperature for a further 2 hours. 60 mmol of N,N-dimethylformamide are then likewise added dropwise at such a rate that the internal temperature always remains below −75° C. When the addition is complete, the reaction solution is allowed to thaw slowly and is hydrolysed at −10° C. by transfer of the reaction solution into ice-water. The mixture is acidified using hydrochloric acid (pH=3) and extracted with tert-butyl methyl ether. The combined organic extracts are washed with water and saturated sodium chloride solution and dried using sodium sulfate. After the solvent has been removed under reduced pressure, the crude product is chromatographed on silica gel with dichloromethane/n-heptane 1:1 as eluent, giving 3,4,5-trifluoro-4′-(4-propylcyclohexyl)biphenyl-2-carbaldehyde in the form of slightly yellowish crystals; m.p. 62° C.

Workup

  1. customdoes not exceed −75° C
  2. additionWhen the addition
  3. extractionextracted with tert-butyl methyl ether
  4. washThe combined organic extracts are washed with water and saturated sodium chloride solution
  5. customdried
  6. customAfter the solvent has been removed under reduced pressure
  7. customthe crude product is chromatographed on silica gel with dichloromethane/n-heptane 1:1 as eluent

Sources & evidence

ORD record
ord-0b8137caf3d7443184c674d1fbc78c56
Source dataset
uspto-grants-2004_09
Patent number
US06793984B2

Reaction notes

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