Hydrochloric Acid → (4E)-5-(2-pyridyl)-4-pentenoic acid

HRID 1741819노트

반응식

HRID 1741819 반응식
[H-].[Na+].[Cl-].[C:4]([CH2:7][CH2:8][CH2:9][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([OH:6])=[O:5].[N:29]1[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=1[CH:35]=O.Cl>CS(C)=O.O>[N:29]1[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=1/[CH:35]=[CH:9]/[CH2:8][CH2:7][C:4]([OH:6])=[O:5]

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 142732-PyridinecarboxaldehydeHCID 24758Sodium hydrideHCID 21180642(3-Carboxypropyl)(triphenyl)phosphanium chloride

생성물 1

HCID 19010766(4E)-5-(2-pyridyl)-4-pentenoic acid수율 24.4%

시약·촉매·용매 2

HCID 679Dimethyl Sulfoxide용매HCID 962Water용매

반응 조건

온도
80 °C

실험 절차

A stirred suspension of sodium hydride (3.04 g; 60% in mineral oil) in dimethyl sulfoxide (100 ml) was heated at 80° C. for 40 minutes. Then the solution was cooled. To the solution was added (3-carboxypropyl)triphenylphosphonium chloride (15.9 g) portionwise at ambient temperature. After 30 minutes, 2-pyridinecarbaldehyde (3.96 g) was added at ambient temperature and then the mixture was stirred for 2 hours. Water was added to the mixture and acidified to pH 5 with 1N hydrochloric acid. The mixture was extracted with ethyl acetate and combined organic layer was washed with brine, dried, and concentrated. The residue was chromatographed on silica gel ethyl acetate:methanol=10:1) to give (4E)-5-(2-pyridyl)-4-pentenoic acid (1.6 g).

후처리

  1. temperatureThen the solution was cooled
  2. extractionThe mixture was extracted with ethyl acetate and combined organic layer
  3. washwas washed with brine
  4. customdried
  5. concentrationconcentrated
  6. customThe residue was chromatographed on silica gel ethyl acetate

출처 및 근거

ORD 기록
ord-645699a344174d648f69bf897431ff3d
출처 데이터셋
uspto-grants-1994_08
특허 번호
US05334716

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