4-Toluenesulfonyl chloride → HCID 58535838, compound

HRID 1941732Notes

Reaction equation

HRID 1941732 reaction equation
[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:15]=[CH:14][C:13]([CH2:16][CH2:17][C:18]3(O)[CH2:23][CH2:22][CH:21]([CH:24]4[CH2:29][CH2:28][CH:27]([CH2:30][CH2:31][CH3:32])[CH2:26][CH2:25]4)[CH2:20][O:19]3)=[C:12]([F:34])[C:11]=2[F:35])=[C:6]([F:36])[C:5]=1[F:37])[CH3:2].C1(C)C=CC(S(Cl)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:15]=[CH:14][C:13]([CH2:16][CH2:17][C:18]3[O:19][CH2:20][CH:21]([CH:24]4[CH2:29][CH2:28][CH:27]([CH2:30][CH2:31][CH3:32])[CH2:26][CH2:25]4)[CH2:22][CH:23]=3)=[C:12]([F:34])[C:11]=2[F:35])=[C:6]([F:36])[C:5]=1[F:37])[CH3:2]

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 58535467HCID 58535467, compound

Product 1

HCID 58535838HCID 58535838, compoundYield 95.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

2-(2-(4′-Ethoxy-2,2′,3,3′-tetrafluorobiphenyl-4-yl)ethyl)-5-(4-propylcyclohexyl)tetrahydro-2H-pyran-2-ol (30) (2.7 g) prepared in the first step was dissolved in toluene (20 ml), and p-toluenesulfonyl chloride (25 mg) was added. A reaction vessel was equipped with a Dean-Stark condenser, and the mixture was refluxed for 3 hours. After the reaction mixture had been cooled, it was washed with a saturated aqueous solution of sodium hydrogencarbonate and water, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to leave 6-(2-(4′-ethoxy-2,2′,3,3′-tetrafluorobiphenyl-4-yl)ethyl)-3-(4-propylcyclohexyl)-3,4-dihydro-2H-pyran (31) (2.5 g) in 95.9% yield.

Workup

  1. customA reaction vessel was equipped with a Dean-Stark condenser
  2. temperaturethe mixture was refluxed for 3 hours
  3. temperatureAfter the reaction mixture had been cooled
  4. washit was washed with a saturated aqueous solution of sodium hydrogencarbonate and water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-f1ccf3a602a74ea885ccbd63f7816ced
Source dataset
uspto-grants-2013_03
Patent number
US08389073B2

Reaction notes

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