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

HRID 483343

반응식

HRID 483343 반응식
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

참가 물질

7

반응물 5

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-e2110da89b014d4c8edcf2be29c74143
출처 데이터셋
uspto-grants-1993_07
특허 번호
US05225422

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