Chloroform → 4-(2-Benzoyloxyethoxy)-6,6'-dimethyl-2,2'-bipyridine

HRID 1586933Notes

Reaction equation

HRID 1586933 reaction equation
[OH:1][CH2:2][CH2:3][O:4][C:5]1[CH:10]=[C:9]([CH3:11])[N:8]=[C:7]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([CH3:18])[N:13]=2)[CH:6]=1.[C:19](Cl)(=[O:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C(Cl)(Cl)Cl>N1C=CC=CC=1>[C:19]([O:1][CH2:2][CH2:3][O:4][C:5]1[CH:10]=[C:9]([CH3:11])[N:8]=[C:7]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([CH3:18])[N:13]=2)[CH:6]=1)(=[O:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 6212ChloroformHCID 7412Benzoyl chlorideHCID 197601174-(2-Hydroxyethoxy)-6,6'-dimethyl-2,2'-bipyridine

Product 1

HCID 197601424-(2-Benzoyloxyethoxy)-6,6'-dimethyl-2,2'-bipyridine

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

4-(2-Hydroxyethoxy)-6,6'-dimethyl-2,2'-bipyridine (24) (1.0 g, 4.1 mmoles) was dissolved in dry pyridine (20 ml), and benzoyl chloride (0.63 g, 4.5 mmoles) was added. After 30 minutes chloroform (50 ml) was added and the solution was extracted with saturated sodium bicarbonate. The chloroform phase was dried and the solvent was evaporated and coevaporated with dry toluene. The product was purified by means of flash chromatography (silica, 0-50% methanol/dichloromethane).

Workup

  1. extractionthe solution was extracted with saturated sodium bicarbonate
  2. dry with materialThe chloroform phase was dried
  3. customthe solvent was evaporated
  4. customThe product was purified by means of flash chromatography (silica, 0-50% methanol/dichloromethane)

Sources & evidence

ORD record
ord-273c8d6b2e764acbb6c7edc8aff1b792
Source dataset
uspto-grants-1993_06
Patent number
US05216134

Reaction notes

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