1,1-Dichloroethane → 3-Acetoxy-2-{1-(methoxycarbonyl)ethoxy}pyridine

HRID 493958노트

반응식

HRID 493958 반응식
N[C:2]1[C:3]([O:8][CH:9]([C:11]([O:13][CH3:14])=[O:12])[CH3:10])=[N:4][CH:5]=[CH:6][CH:7]=1.ClC(Cl)C.N([O:21][C:22]([CH3:25])(C)C)=O.CCCCC.C[O:32]CCOC>>[C:22]([O:21][C:2]1[C:3]([O:8][CH:9]([C:11]([O:13][CH3:14])=[O:12])[CH3:10])=[N:4][CH:5]=[CH:6][CH:7]=1)(=[O:32])[CH3:25]

참가 물질

6

반응물 5

HCID 63651,1-DichloroethaneHCID 8003PentaneHCID 80711,2-Dimethoxyethane2회HCID 10906Tert-Butyl nitriteHCID 219335303-Amino-2-{1-(methoxycarbonyl)ethoxy}pyridine

생성물 1

HCID 219335453-Acetoxy-2-{1-(methoxycarbonyl)ethoxy}pyridine

실험 절차

First, 1.5 ml of a boron trifluoride diethyl ether complex was added dropwise to a mixture of 1.1 g of 3-amino-2-{1 -(methoxycarbonyl)ethoxy}pyridine, 1 ml of 1,2-dimethoxyethane, and 1 ml of dichloroethane at −10° C. After stirring at the same temperature for 10 minutes, a solution of 0.8 ml of t-butyl nitrite in 1 ml of 1,2-dimethoxyethane was added dropwise to the reaction mixture at −5° C. or lower. After stirring at the same temperature for 30 minutes, n-pentane was poured into the mixture. The lower one of the two layers separated was dissolved in acetic anhydride, and the solution was stirred at 70° C. for 1 hour. After the solvent was distilled out, the residue was subjected to silica gel chromatography to give 0.34 g of 3-acetoxy-2-{1-(methoxycarbonyl)ethoxy}pyridine.

후처리

  1. stirringAfter stirring at the same temperature for 30 minutes
  2. customThe lower one of the two layers separated
  3. dissolutionwas dissolved in acetic anhydride
  4. stirringthe solution was stirred at 70° C. for 1 hour
  5. distillationAfter the solvent was distilled out

출처 및 근거

ORD 기록
ord-9e972da0d9944811b950fe51fe27ae29
출처 데이터셋
uspto-grants-2009_05
특허 번호
US07538072B2

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