Tetrahydrofuran → Ethyl 6-(3-chloropropyl)pyridine-2-carboxylate

HRID 483343

Reaction equation

HRID 483343 reaction equation
S(Cl)(Cl)=[O:2].[CH3:5][C:6]1([CH3:11])COC=[N:7]1.C([Li])C[CH2:14][CH3:15].C1(O[CH2:24][CH2:25][Cl:26])C=CC=CC=1.[O:27]1[CH2:31][CH2:30][CH2:29][CH2:28]1>ClCCl>[Cl:26][CH2:25][CH2:24][CH2:5][C:6]1[N:7]=[C:30]([C:31]([O:27][CH2:14][CH3:15])=[O:2])[CH:29]=[CH:28][CH:11]=1

Participants

7

Reactant 5

HCID 8028TetrahydrofuranHCID 12156Benzene, (2-chloroethoxy)-HCID 24386Thionyl ChlorideHCID 1216304,4-Dimethyl-2-oxazolineHCID 178418339Butyllithium

Product 1

HCID 19752437Ethyl 6-(3-chloropropyl)pyridine-2-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 6-methylpyridine-2-carboxylic acid (13.7 g, 100 mmol) and thionyl chloride (40 ml) was stirred at 70° C. for 1 hour. The mixture was dried, and dichloromethane (40 ml) was added to the residue. The solution was added to a dichloromethane solution of 2-amino-2-methyl-propanol (36.0 g, 400 mmol), and stirred. The mixture was washed with water, and dried over anhydrous magnesium sulfate. The extract was concentrated and chromatographed on silica gel to give an amide compound. 4,4-Dimethyl-2-oxazoline compound was obtained by reacting the amide compound and thionyl chloride in dichloromethane. 4,4-Dimethyl-2-oxazoline compound was reacted with n-butyl lithium at -78° C. in anhydrous tetrahydrofuran, and chloroethyl phenyl ether (782 mg, 5 mmol) was added. Purified alkylated compound was treated with ethanol saturated with HCl to give ethyl 6-(3-chloropropyl)pyridine-2-carboxylate.

Workup

  1. customPurified
  2. additionwas treated with ethanol saturated with HCl

Sources & evidence

ORD record
ord-e2110da89b014d4c8edcf2be29c74143
Source dataset
uspto-grants-1993_07
Patent number
US05225422

Linked notes

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