Sodium hydride → HCID 20535521, compound

HRID 1156209Notes

Reaction equation

HRID 1156209 reaction equation
[H-].[Na+].[CH3:3][C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][CH:12]=1)[CH2:7][CH2:8][OH:9].Cl[C:14]1[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][N:15]=1>CN(C)C=O>[CH3:3][C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][CH:12]=1)[CH2:7][CH2:8][O:9][C:14]1[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][N:15]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 746483-MethylbenzeneethanolHCID 783082-Chloro-5-nitropyridine

Product 1

HCID 20535521HCID 20535521, compoundYield 79.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of 4.8 g of sodium hydride (50% oily suspension) in 130 ml of dimethylformamide, was added dropwise 13.6 g of 3-methylphenethyl alcohol in 20 minutes, and the resultant mixture was heated at 60° C. for 2 hours. After cooling, a solution of 15.9 g of 2-chloro-5-nitropyridine in 80 ml of dimethylformamide was added dropwise thereto at a temperature below 20° C. under ice-cooling. After standing at room temperature overnight, the reaction mixture was poured into ice water, followed by extraction with ethyl acetate. The extracts were washed with water and dried over magnesium sulfate. The oily products were purified by column chromatography on silica gel using benzene as an eluent to give 20.4 g of 2-(3-methylphenethyloxy)-5-nitropyridine as white crystals. M.P., 73.5°-74.5° C.

Workup

  1. temperatureAfter cooling
  2. temperatureat a temperature below 20° C. under ice-cooling
  3. extractionfollowed by extraction with ethyl acetate
  4. washThe extracts were washed with water
  5. dry with materialdried over magnesium sulfate
  6. customThe oily products were purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-9b7622cbcca349bf846b9a65581ba375
Source dataset
uspto-grants-1982_06
Patent number
US04334912

Reaction notes

Loading…