Picolyl chloride → HCID 178420297, compound

HRID 1679023Notes

Reaction equation

HRID 1679023 reaction equation
[OH:1][C@H:2]1[CH2:7][O:6][C@@H:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[O:4][CH2:3]1.[H-].[Na+].Cl[CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=1>C1C=CC=CC=1>[C:8]1([C@H:5]2[O:4][CH2:3][C@@H:2]([O:1][CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=3)[CH2:7][O:6]2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 23393Picolyl chlorideHCID 24758Sodium hydrideHCID 178521647HCID 178521647, compound

Product 1

HCID 178420297HCID 178420297, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of cis-5-hydroxy-2-phenyl-1,3-dioxane in 300 ml of benzene was treated with 4.45 g of 54% sodium hydride and the mixture stirred at ambient temperature until gas evolution ceased. To this mixture was added a solution of 2-chloromethylpyridine (obtained by extracting with benzene a carefully neutralized solution of 18.04 g of 2-chloromethylpyridine hydrochloride in 50 ml of water, then drying the benzene extracts) and the mixture was heated under reflux for 19 hours. The mixture was filtered and the filtrate washed with water and dried over sodium sulfate. Removal of the benzene under reduced pressure gave yellow solid which on recrystallization from benzene-petroleum ether (65°-110°) gave 14.2 g of cis-2-phenyl-5-(2-pyridyl)methoxy-1,3 -dioxane, m.p. 95°-98°. The nmr spectrum was consistent with the assigned structure and indicated pure cis isomer.

Workup

  1. customobtained
  2. extractionby extracting with benzene a carefully neutralized solution of 18.04 g of 2-chloromethylpyridine hydrochloride in 50 ml of water
  3. dry with materialdrying the benzene extracts) and the mixture
  4. temperaturewas heated
  5. temperatureunder reflux for 19 hours
  6. filtrationThe mixture was filtered
  7. washthe filtrate washed with water
  8. dry with materialdried over sodium sulfate
  9. customRemoval of the benzene under reduced pressure
  10. customgave yellow solid which
  11. customon recrystallization from benzene-petroleum ether (65°-110°)

Sources & evidence

ORD record
ord-1231f0080c0248af94c30617a938e50e
Source dataset
uspto-grants-1978_03
Patent number
US04077982

Reaction notes

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