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

HRID 483343

反応式

HRID 483343 の反応式
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

参加物

7

反応物 5

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-e2110da89b014d4c8edcf2be29c74143
出典データセット
uspto-grants-1993_07
特許番号
US05225422

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