Pyridine N-Oxide → Ethyl 5-oxopentanoate

HRID 1381723

반응식

HRID 1381723 반응식
Br[CH2:2][CH2:3][CH2:4][CH2:5][C:6]([O:8][CH2:9][CH3:10])=[O:7].C(=O)(O)[O-:12].[Na+].[N+]1([O-])C=CC=CC=1>C1(C)C=CC=CC=1>[O:12]=[CH:2][CH2:3][CH2:4][CH2:5][C:6]([O:8][CH2:9][CH3:10])=[O:7]

참가 물질

5

반응물 3

HCID 12753Pyridine N-OxideHCID 84580Ethyl 5-bromovalerateHCID 516892Sodium Bicarbonate

생성물 1

HCID 11137279Ethyl 5-oxopentanoate수율 48.7%

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

Ethyl 5-bromopentanoate (42 g), sodium bicarbonate (34 g) and pyridine N-oxide (38 g) in toluene (250 ml) are heated together under reflux in an atmosphere of nitrogen with vigorous stirring for 9 hours. After cooling, the product is partitioned with water (400 ml). The toluene layer is separated and the aqueous layer is extracted with a further amount of toluene (100 ml). The combined toluene extracts are dried over magnesium sulphate and the toluene removed by fractional distillation. The residue is distilled under vacuum to give ethyl 5-oxopentanoate as a colourless oil (14.1 g), m.s. M+ 144.

후처리

  1. temperatureunder reflux in an atmosphere of nitrogen
  2. temperatureAfter cooling
  3. customthe product is partitioned with water (400 ml)
  4. customThe toluene layer is separated
  5. extractionthe aqueous layer is extracted with a further amount of toluene (100 ml)
  6. dry with materialThe combined toluene extracts are dried over magnesium sulphate
  7. customthe toluene removed by fractional distillation
  8. distillationThe residue is distilled under vacuum

출처 및 근거

ORD 기록
ord-7941e9fff64245f088b3da5d5a29cb3a
출처 데이터셋
uspto-grants-1989_02
특허 번호
US04803289

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