4-Toluenesulfonyl chloride → HCID 18411885, compound

HRID 1591440Notes

Reaction equation

HRID 1591440 reaction equation
[F:1][C:2]([F:13])([F:12])[C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[CH2:6][CH2:7][OH:8].[C:14]1([CH3:24])[CH:19]=[CH:18][C:17]([S:20](Cl)(=[O:22])=[O:21])=[CH:16][CH:15]=1.C(N(CC)CC)C>CCOCC>[S:20]([C:17]1[CH:18]=[CH:19][C:14]([CH3:24])=[CH:15][CH:16]=1)([O:8][CH2:7][CH2:6][C:5]1[CH:9]=[CH:10][CH:11]=[C:3]([C:2]([F:12])([F:13])[F:1])[CH:4]=1)(=[O:22])=[O:21]

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 959263-(Trifluoromethyl)phenethylic alcohol

Product 1

HCID 18411885HCID 18411885, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of 10.0 g (52.6 mmol) of 3-(trifluoromethyl)phenethyl alcohol in 75 mL of ether under nitrogen was treated with 10.53 g (55.2 mmol, 1.05 eq) p-toluenesulfonyl chloride. The solution was cooled to 0° and treated with 7.67 mL (5.57 g, 55.0 mmol, 1.05 eq) of triethylamine. The mixture was stirred at 0° for 30 minutes then warmed to room temperature and stirred for 16 hours. The precipitate was removed by filtration and washed with ether. The combined filtrate and ether wash were evaporated under vacuum. The residue was redissolved in ethyl acetate and washed with 0.5N HCl and brine; the organic layer was removed, dried over sodium sulfate, filtered and concentrated under vacuum. Purification by flash chromatography on silica, eluting with 30% ethyl acetate/hexane, afforded 15.14 g (44.0 mmol, 84%) of the product. 1H NMR (200 MHz, CDCl3): 2.44 (s,3H), 3.03 (t,7 Hz,2H), 4.26 (t,7 Hz,2H), 7.2-7.5 (m,6H), 7.66 (d,8 Hz,2H). FAB-MS: calculated for C16H15F3SO3 344; found 345 (M+H, 8%).

Workup

  1. temperatureThe solution was cooled to 0°
  2. stirringstirred for 16 hours
  3. customThe precipitate was removed by filtration
  4. washwashed with ether
  5. washThe combined filtrate and ether wash
  6. customwere evaporated under vacuum
  7. dissolutionThe residue was redissolved in ethyl acetate
  8. washwashed with 0.5N HCl and brine
  9. customthe organic layer was removed
  10. dry with materialdried over sodium sulfate
  11. filtrationfiltered
  12. concentrationconcentrated under vacuum
  13. customPurification by flash chromatography on silica
  14. washeluting with 30% ethyl acetate/hexane

Sources & evidence

ORD record
ord-085bd0b686874dc3b26417886a133aad
Source dataset
uspto-grants-1993_04
Patent number
US05206235

Reaction notes

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