Pyridine → HCID 19889944, compound

HRID 653690Notes

Reaction equation

HRID 653690 reaction equation
S(Cl)([Cl:3])=O.[CH:5]1([CH2:15]O)[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH2:8][CH2:7][O:6]1.N1C=CC=CC=1>C1C=CC=CC=1>[CH:5]1([CH2:15][Cl:3])[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH2:8][CH2:7][O:6]1

Participants

5

Reactant 3

HCID 1049PyridineHCID 24386Thionyl ChlorideHCID 13486958HCID 13486958, compound

Product 1

HCID 19889944HCID 19889944, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

8.4 g (70.6 mmol) of thionyl chloride was dropwise added to a solution of 10 g (61 mmol) of (isochroman-1-yl)methanol [J. Med. Chem., 28, 1026 (1985)] and 5 g (63 mmol) of anhydrous pyridine in dried benzene, and the resulting mixture was heated under reflux for 2 hours. Excessive amounts of thionyl chloride and benzene were evaporated, and the residue was dissolved in ether. The ethereal solution was washed with water and dried, and the solvent was then evaporated. The residue was distilled under reduced pressure (140° C./20 mmHg) to give 10.9 g (98%) of the desired compound as an oily.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureunder reflux for 2 hours
  3. customExcessive amounts of thionyl chloride and benzene were evaporated
  4. dissolutionthe residue was dissolved in ether
  5. washThe ethereal solution was washed with water
  6. customdried
  7. customthe solvent was then evaporated
  8. distillationThe residue was distilled under reduced pressure (140° C./20 mmHg)

Sources & evidence

ORD record
ord-676beb11577c4a93b8019a9569666c0c
Source dataset
uspto-grants-1992_07
Patent number
US05128369

Reaction notes

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