5-Butyl-2-methylpyridine → HCID 53825401, compound

HRID 2072628Notes

Reaction equation

HRID 2072628 reaction equation
C1([Li])C=CC=CC=1.[CH2:8]([C:12]1[CH:13]=[CH:14][C:15]([CH3:18])=[N:16][CH:17]=1)[CH2:9][CH2:10][CH3:11].[CH2:19]([O:21][C:22]1[CH:29]=[CH:28][C:25]([CH2:26]Cl)=[CH:24][CH:23]=1)[CH3:20]>C1CCCCC1.C(OCC)C.C(OCC)C>[CH2:19]([O:21][C:22]1[CH:29]=[CH:28][C:25]([CH2:26][CH2:18][C:15]2[CH:14]=[CH:13][C:12]([CH2:8][CH2:9][CH2:10][CH3:11])=[CH:17][N:16]=2)=[CH:24][CH:23]=1)[CH3:20]

Participants

6

Reactant 3

HCID 697045-Butyl-2-methylpyridineHCID 20639711-(Chloromethyl)-4-EthoxybenzeneHCID 178506676HCID 178506676, compound

Product 1

HCID 53825401HCID 53825401, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent3×HCID 21895417Cyclohexane diethyletherSolvent

Procedure

46 ml of a 2.2 molar solution of phenyllithium in cyclohexane/diethyl ether (7:3) are added with ice cooling to a solution of 14.9 g of 5-butyl-2-picoline in 50 ml of diethyl ether. After 1 hour of stirring, 15.9 g of 4-ethoxybenzyl chloride in 50 ml of diethyl ether are then added at room temperature, and the ether starts to boil. The reaction mixture is poured onto ice after 1 hour, and the organic phase is worked up. Separation by column chromatography (silica gel, toluene) and recrystallization gives 2-(p-ethoxyphenylethyl)-5-butylpyridine.

Workup

  1. additionThe reaction mixture is poured onto ice after 1 hour
  2. customSeparation
  3. customby column chromatography (silica gel, toluene) and recrystallization

Sources & evidence

ORD record
ord-5f3f2c52eb6d44a0bbf592a8e2021ce0
Source dataset
uspto-grants-1990_04
Patent number
US04913837

Reaction notes

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