Pyridine → 2-Furanacetic acid 2-bromoethyl ester

HRID 1580498

반응식

HRID 1580498 반응식
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][C:7]([OH:9])=[O:8].[Cl-].ClC=[N+](C)C.[Br:16][CH2:17][CH2:18]O.N1C=CC=CC=1>C(Cl)Cl>[Br:16][CH2:17][CH2:18][O:8][C:7](=[O:9])[CH2:6][C:2]1[O:1][CH:5]=[CH:4][CH:3]=1

참가 물질

6

반응물 4

HCID 1049PyridineHCID 108982-BromoethanolHCID 75974Furan-2-acetic acidHCID 77311Chloro-N,N-dimethylformiminium chloride

생성물 1

HCID 537168022-Furanacetic acid 2-bromoethyl ester

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

A solution of 15.12 g of furanacetic acid in 120 ml of methylene chloride is cooled to 0°; 15.6 g of chloromethylene-dimethylammonium chloride are added and the mixture is stirred for 10 minutes while cooling with ice. A solution of 30 g of 2-bromoethanol and 19.4 ml of pyridine in 60 ml of methylene chloride is then added dropwise with stirring and the reaction mixture is left to stand for 20 minutes while cooling with ice and for 1 hour at room temperature. The solution is extracted three times with a 5% aqueous sodium bicarbonate solution and once with a saturated aqueous sodium chloride solution, dried over sodium sulphate and distilled under reduced pressure. The 2-furanacetic acid 2-bromoethyl ester is obtained at 76°/0.25 mm; infrared absorption spectrum (in methylene chloride): characteristic bands at 3,44μ, 5,72μ, 6,10μ, 7,49μ, 8,20μ, 8,68μ, 9,31μ and 9,86μ.

후처리

  1. temperaturewhile cooling with ice
  2. stirringwith stirring
  3. waitthe reaction mixture is left
  4. waitto stand for 20 minutes
  5. extractionThe solution is extracted three times with a 5% aqueous sodium bicarbonate solution
  6. dry with materialonce with a saturated aqueous sodium chloride solution, dried over sodium sulphate
  7. distillationdistilled under reduced pressure

출처 및 근거

ORD 기록
ord-cf633b8f6bed472786729957555bfb4d
출처 데이터셋
uspto-grants-1976_01
특허 번호
US03932465

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