4-Toluenesulfonyl chloride → HCID 13151494, compound

HRID 1648860Notes

Reaction equation

HRID 1648860 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:12][CH:11]([CH2:13][OH:14])[CH2:10][O:9]2)=[CH:4][CH:3]=1.[S:15](Cl)([C:18]1[CH:24]=[CH:23][C:21]([CH3:22])=[CH:20][CH:19]=1)(=[O:17])=[O:16]>N1C=CC=CC=1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]2[CH2:12][CH:11]([CH2:13][O:14][S:15]([C:18]3[CH:24]=[CH:23][C:21]([CH3:22])=[CH:20][CH:19]=3)(=[O:17])=[O:16])[CH2:10][O:9]2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 13151493HCID 13151493, compound

Product 1

HCID 13151494HCID 13151494, compoundYield 87.2%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
4 °C

Procedure

2-(4-Fluorophenyl)-4-(hydroxymethyl)tetrahydrofuran (21 g) is dissolved in 170 ml of pyridine whereupon 24.4 g of tosyl chloride is added below 4° C., and the resulting mixture is stirred at 4° C. for 1 hour and then at room temperature for 4 hours. The pyridine is then distilled off at room temperature under reduced pressure. Water is added to the residue and extracted with ethyl acetate. The extract is washed twice with dilute hydrochloric acid and once with water and dried over magnesium sulfate, and the solvent is distilled off under reduced pressure. To the residue are added n-hexane and isopropyl ether to give 32.7 g of 2-(4-fluorophenyl)-4-(tosyloxymethyl)tetrahydrofuran. This tosyl compound is recrystallized repeatedly from isopropanol to give cis-2-(4-fluorophenyl)-4-tosyloxymethyl)tetrahydrofuran as colorless needles, melting at 75°-76.5° C., and recrystallized from ethanol to give the trans-isomer as colorless needles, melting at 55°-57° C.

Workup

  1. additionis added below 4° C.
  2. waitat room temperature for 4 hours
  3. distillationThe pyridine is then distilled off at room temperature under reduced pressure
  4. additionWater is added to the residue
  5. extractionextracted with ethyl acetate
  6. washThe extract is washed twice with dilute hydrochloric acid and once with water
  7. dry with materialdried over magnesium sulfate
  8. distillationthe solvent is distilled off under reduced pressure
  9. additionTo the residue are added n-hexane and isopropyl ether

Sources & evidence

ORD record
ord-49c702bd1244449fb4d0374ad3740e3f
Source dataset
uspto-grants-1983_11
Patent number
US04414216

Reaction notes

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