Pyridine → HCID 54390883, compound

HRID 1078031Notes

Reaction equation

HRID 1078031 reaction equation
[F:1][C@H:2]([CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10])[CH2:3][OH:4].N1C=CC=CC=1.[S:17](Cl)([C:20]1[CH:26]=[CH:25][C:23]([CH3:24])=[CH:22][CH:21]=1)(=[O:19])=[O:18]>O>[S:17]([C:20]1[CH:26]=[CH:25][C:23]([CH3:24])=[CH:22][CH:21]=1)([O:4][CH2:3][C@H:2]([F:1])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10])(=[O:19])=[O:18]

Participants

5

Reactant 3

HCID 1049PyridineHCID 73974-Toluenesulfonyl chlorideHCID 10855629(R)-(+)-2-fluorooctanol

Product 1

HCID 54390883HCID 54390883, compoundYield 93.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A reaction vessel was charged with 10.0 g of (2R)-2fluorooctanol and 25 ml of pyridine, and 13.0 g of tosyl chloride was added with stirring at 0°-5° C. After the reaction was effected for 6 hours, the mixture was poured into water and extracted with 100 ml of benzene. The resultant solution in benzene was washed sequentially with water, an aqueous solution of NaHCO3 and water in that order, and dried over Glauber's salt. The solvent was distilled off to obtain 19.0 g (yield 92.6%) of crude (2R)-2-fluorooctyl tosylate as the residue.

Workup

  1. additionwas added
  2. extractionextracted with 100 ml of benzene
  3. washThe resultant solution in benzene was washed sequentially with water
  4. dry with materialan aqueous solution of NaHCO3 and water in that order, and dried over Glauber's salt
  5. distillationThe solvent was distilled off

Sources & evidence

ORD record
ord-7092816a216d428eb96c78ed3903ba42
Source dataset
uspto-grants-1996_08
Patent number
US05545747

Reaction notes

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