Pyridine → 3-(2-Fluorophenyl)propyl 4-methylbenzenesulfonate

HRID 355951Notes

Reaction equation

HRID 355951 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][CH2:9][CH2:10][OH:11].N1C=CC=CC=1.[C:18]1([CH3:28])[CH:23]=[CH:22][C:21]([S:24](Cl)(=[O:26])=[O:25])=[CH:20][CH:19]=1>CCOCC>[S:24]([C:21]1[CH:22]=[CH:23][C:18]([CH3:28])=[CH:19][CH:20]=1)([O:11][CH2:10][CH2:9][CH2:8][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[F:1])(=[O:26])=[O:25]

Participants

5

Reactant 3

HCID 1049PyridineHCID 73974-Toluenesulfonyl chlorideHCID 126185173-(2-Fluorophenyl)propan-1-ol

Product 1

HCID 224494783-(2-Fluorophenyl)propyl 4-methylbenzenesulfonate

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

17.75 gm of the compound prepared in (3) above was dissolved into 200 ml of dry pyridine. To this was slowly added 24.25 gm of p-toluenesulfonyl chloride at 0° C. and the mixture was stirred for 3 hours at room temperature. After the addition of 300 ml of ether, the mixture was washed with water, followed by the addition of 6N hydrochloric acid to acidify it and washing with saturated brine. The product was dried over anhydrous sodium sulfate and the solvent was evaporated to obtain 31.3 gm of the title compound.

Workup

  1. customat 0° C.
  2. washthe mixture was washed with water
  3. additionfollowed by the addition of 6N hydrochloric acid
  4. washwashing with saturated brine
  5. dry with materialThe product was dried over anhydrous sodium sulfate
  6. customthe solvent was evaporated

Sources & evidence

ORD record
ord-74d4ccf56cbb483da4bd892d65a2305a
Source dataset
uspto-grants-1998_11
Patent number
US05834476

Reaction notes

Loading…