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

HRID 1741819ノート

反応式

HRID 1741819 の反応式
[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]

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 679Dimethyl Sulfoxide溶媒HCID 962Water溶媒

反応条件

温度
80 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-645699a344174d648f69bf897431ff3d
出典データセット
uspto-grants-1994_08
特許番号
US05334716

反応ノート

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