Water → Methyl 5-(benzyloxy)-6-chloronicotinate

HRID 709795노트

반응식

HRID 709795 반응식
[Cl:1][C:2]1[C:11]([OH:12])=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][N:3]=1.[H-].[Na+].[CH2:15](Br)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.O>CN(C=O)C>[CH2:15]([O:12][C:11]1[C:2]([Cl:1])=[N:3][CH:4]=[C:5]([CH:10]=1)[C:6]([O:8][CH3:9])=[O:7])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 46941479Methyl 6-chloro-5-hydroxynicotinate

생성물 1

HCID 71496987Methyl 5-(benzyloxy)-6-chloronicotinate수율 38.6%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
0 °C

실험 절차

To a solution of methyl 6-chloro-5-hydroxynicotinate (10.5 g) in DMF (80 mL) was added 60% sodium hydride (2.80 g) at 0° C., and the mixture was stirred at 0° C. for 0.5 hr. Benzyl bromide (10.5 g) was added, and the mixture was stirred at room temperature for 20 hr. The reaction mixture was poured into water, and the precipitate was collected by filtration. The crude crystals were purified by silica gel column chromatography (petroleum ether/THF) to give the title compound (6.00 g) as a white solid.

후처리

  1. stirringthe mixture was stirred at room temperature for 20 hr
  2. filtrationthe precipitate was collected by filtration
  3. customThe crude crystals were purified by silica gel column chromatography (petroleum ether/THF)

출처 및 근거

ORD 기록
ord-dfd1e4923bb4438c84b11435905ef818
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09181186B2

반응 노트

불러오는 중…