p-Toluenesulfonic acid → 4-fluorophenyl-4-(2-((tetrahydro-2H-pyran-2-yl)oxy)ethoxy)phenyl methanone

HRID 240211Notes

Reaction equation

HRID 240211 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH2:17][CH2:18][OH:19])=[CH:12][CH:11]=2)=[O:9])=[CH:4][CH:3]=1.[O:20]1[CH:25]=[CH:24][CH2:23][CH2:22][CH2:21]1.C1(C)C=CC(S(O)(=O)=O)=CC=1>ClCCl>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH2:17][CH2:18][O:19][CH:21]3[CH2:22][CH2:23][CH2:24][CH2:25][O:20]3)=[CH:12][CH:11]=2)=[O:9])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 80803,4-dihydro-2H-pyranHCID 67170561(4-Fluorophenyl)(4-(2-hydroxyethoxy)phenyl)methanone

Product 1

HCID 676061064-fluorophenyl-4-(2-((tetrahydro-2H-pyran-2-yl)oxy)ethoxy)phenyl methanone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In an oven-dried flask placed under a nitrogen atmosphere, the product of Step 1 (121 g) and 3,4-dihydro-2H-pyran (106 mL) were stirred in dichloromethane (1100 mL). To this was added p-toluenesulfonic acid (4.4 g). The reaction mixture was stirred at room temperature for 2 hours. It was then transferred to a separatory funnel and washed with a saturated aqueous solution of sodium bicarbonate (1 L), dried over sodium sulfate and concentrated by rotary evaporation to yield an oil. 160 grams of 4-fluorophenyl-4-(2-((tetrahydro-2H-pyran-2-yl)oxy)ethoxy)phenyl methanone was isolated. It was used in the next reaction as is without further purification.

Workup

  1. customIn an oven-dried flask placed under a nitrogen atmosphere
  2. customIt was then transferred to a separatory funnel
  3. washwashed with a saturated aqueous solution of sodium bicarbonate (1 L)
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated by rotary evaporation
  6. customto yield an oil

Sources & evidence

ORD record
ord-8829611b735e433ea2d0c71ebf441b62
Source dataset
uspto-grants-2014_02
Patent number
US08647538B2

Reaction notes

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