Hydrochloric Acid → HCID 178445638, compound

HRID 2268710Notes

Reaction equation

HRID 2268710 reaction equation
[H-].[Na+].[Cl:3][C:4]1[C:9]([F:10])=[C:8]([CH3:11])[CH:7]=[CH:6][C:5]=1[C:12]1[CH:17]=[CH:16][C:15]([OH:18])=[C:14]([F:19])[C:13]=1[F:20].[CH2:21]([C@H:25]1[CH2:30][CH2:29][C@H:28]([C@H:31]2[CH2:36][CH2:35][C@H:34]([CH2:37]I)[CH2:33][CH2:32]2)[CH2:27][CH2:26]1)[CH2:22][CH2:23][CH3:24].Cl>CN(C=O)C>[Cl:3][C:4]1[C:9]([F:10])=[C:8]([CH3:11])[CH:7]=[CH:6][C:5]=1[C:12]1[CH:17]=[CH:16][C:15]([O:18][CH2:37][C@H:34]2[CH2:35][CH2:36][C@H:31]([C@H:28]3[CH2:29][CH2:30][C@H:25]([CH2:21][CH2:22][CH2:23][CH3:24])[CH2:26][CH2:27]3)[CH2:32][CH2:33]2)=[C:14]([F:19])[C:13]=1[F:20]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 18332051HCID 18332051, compoundHCID 178445636HCID 178445636, compound

Product 1

HCID 178445638HCID 178445638, compoundYield 61.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

In a mixture of 0.7 g (60% oiliness, corresponding to 17.6 mmol) of sodium hydride and 5 ml of DMF was added by drops a solution of 4.0 g (14.7 mmol) of the 2′-chloro-2,3,3′-trifluoro-4-hydroxy-4′-methylbiphenyl in 20 ml of DMF at room temperature and stirred at the same temperature for 1 hour. Subsequently, a solution of 8.0 g (22.0 mmol) of trans-4-(trans-4-butylcyclohexyl)-1-iodomethylcyclohexane in 20 ml of DMF was added by drops to the reaction solution at room temperature, stirred at the same temperature for 1 hour, and then refluxed for 3 hours. After termination of the reaction, the reaction solution was poured into 50 ml of a diluted hydrochloric acid and extracted with 150 ml of toluene. The organic layer thus obtained was washed with a diluted aqueous sodium hydroxide solution thrice and water thrice, and then dried over anhydrous magnesium sulfate. The solvent was distilled off under a reduced pressure and the residue was subjected to silica gel column chromatography (eluent: heptane/toluene=7/3) to obtain 4.6 g of a crude 2′-chloro-2,3,3′-trifluoro-4′-methyl-4-((trans-4-(trans-4-butylcyclohexyl)cyclohexyl)methoxy)biphenyl. This product was recrystallized from a mixed solvent of ethanol/ethyl acetate to obtain 3.3 g of the subject compound. (Yield: 44.6%)

Workup

  1. stirringstirred at the same temperature for 1 hour
  2. temperaturerefluxed for 3 hours
  3. customAfter termination of the reaction
  4. extractionextracted with 150 ml of toluene
  5. customThe organic layer thus obtained
  6. washwas washed with a diluted aqueous sodium hydroxide solution thrice and water thrice
  7. dry with materialdried over anhydrous magnesium sulfate
  8. distillationThe solvent was distilled off under a reduced pressure

Sources & evidence

ORD record
ord-eade1db4b3414433b06ce488620407f8
Source dataset
uspto-grants-2001_12
Patent number
US06329027B1

Reaction notes

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