Toluene → HCID 178520916, compound

HRID 486365Notes

Reaction equation

HRID 486365 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:9]2[CH:14]=[CH:13][C:12]([CH:15]3[CH2:20][CH2:19][CH:18]([CH:21]4OCCC[O:22]4)[CH2:17][CH2:16]3)=[CH:11][N:10]=2)[CH:5]=[CH:6][C:7]=1[F:8].C1(C)C=CC=CC=1.C(=O)([O-])[O-].[Na+].[Na+]>C(O)=O>[F:1][C:2]1[CH:3]=[C:4]([C:9]2[CH:14]=[CH:13][C:12]([C@H:15]3[CH2:16][CH2:17][C@H:18]([CH:21]=[O:22])[CH2:19][CH2:20]3)=[CH:11][N:10]=2)[CH:5]=[CH:6][C:7]=1[F:8]

Participants

5

Reactant 3

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 19094914HCID 19094914, compound

Product 1

HCID 178520916HCID 178520916, compoundYield 8%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

A mixture of 1.65 g of 2-(3,4-difluorophenyl)-5-[4-(1,3-dioxan-2-yl)cyclohexyl]pyridine, 15 ml of toluene and 10 ml of formic acid is stirred at room temperature for 10 hours and subsequently carefully neutralized to pH 7 with saturated sodium carbonate solution. The aqueous phase is separated and extracted twice with toluene, the organic phases are combined, washed with water, dried over sodium sulphate and evaporated. The residue is dissolved in 15 ml of methanol and added dropwise to 10 ml of 0.1N methanolic potassium hydroxide solution cooled to 0° C. The mixture is stirred at 0° C. for 1 hour, poured on to 40 ml of ice-water and extracted three times with 25 ml of diethyl ether each time. The organic phases are combined, washed neutral with water, dried over sodium sulphate and, after evaporation, give trans-4[2-(3,4-difluorophenyl)-5-pyridyl]-cyclohexanecarboxaldehyde (cis content about 8%).

Workup

  1. customThe aqueous phase is separated
  2. extractionextracted twice with toluene
  3. washwashed with water
  4. dry with materialdried over sodium sulphate
  5. customevaporated
  6. dissolutionThe residue is dissolved in 15 ml of methanol
  7. additionadded dropwise to 10 ml of 0.1N methanolic potassium hydroxide solution
  8. temperaturecooled to 0° C
  9. stirringThe mixture is stirred at 0° C. for 1 hour
  10. additionpoured on to 40 ml of ice-water
  11. extractionextracted three times with 25 ml of diethyl ether each time
  12. washwashed neutral with water
  13. dry with materialdried over sodium sulphate
  14. customafter evaporation

Sources & evidence

ORD record
ord-a16ac0ecbcf0434c863cc20da028bc45
Source dataset
uspto-grants-1994_03
Patent number
US05292452

Reaction notes

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