Morpholine → Ethyl 2,4-dimethyl[1,1'-biphenyl]-3-carboxylate

HRID 1153842

反応式

HRID 1153842 の反応式
[CH3:1][C:2]1[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[C:6]([CH3:13])OC(=O)[CH:3]=1.[C:15]1([CH:21]=[CH:22]N2CCOCC2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.N1CCOCC1>C1(C)C=CC=CC=1>[CH3:13][C:6]1[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[C:2]([CH3:3])[CH:1]=[CH:22][C:21]=1[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

参加物

5

反応物 3

HCID 8083MorpholineHCID 76918ethyl 4,6-dimethyl-2-oxo-2H-pyran-5-carboxylateHCID 544920984-(2-Phenylethenyl)morpholine

生成物 1

HCID 13126289Ethyl 2,4-dimethyl[1,1'-biphenyl]-3-carboxylate収率 18.1%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒2 回

実験手順

Under a dry nitrogen atmosphere a solution of commercial ethyl 4,6-dimethyl-2-oxo-2H-pyran-5-carboxylate (19.6 g, 0.1 mole) in toluene (20 ml) was added dropwise to a stirred solution of 4-(2-phenylethenyl)morpholine (14.3 g, 0.076 mole) in toluene (200 ml). Preparation of the morpholine derivative is described in U.S. Pat. No. 3,922,237. After the addition, the reaction mixture was heated at reflux for approximately 20 hours. The reaction mixture was then cooled and concentrated under reduced pressure, leaving a residue. The residue was heated at 170° under a dry nitrogen atmosphere for 3.5 hours, allowed to cool to room temperature, and then filtered. The filtrate was purified by column chromatography on silica gel, elution first with n-hexane: ethyl acetate, and finally ethyl acetate, to give ethyl 2,4-dimethyl-[1,1'-biphenyl]-3-carboxylate (3.5 g) as a yellow oil.

後処理

  1. additionAfter the addition
  2. temperaturethe reaction mixture was heated
  3. temperatureat reflux for approximately 20 hours
  4. temperatureThe reaction mixture was then cooled
  5. concentrationconcentrated under reduced pressure
  6. customleaving a residue
  7. temperatureThe residue was heated at 170° under a dry nitrogen atmosphere for 3.5 hours
  8. filtrationfiltered
  9. customThe filtrate was purified by column chromatography on silica gel, elution first with n-hexane

出典と根拠

ORDレコード
ord-e52eceddde834449b16106a075d0035c
出典データセット
uspto-grants-1984_12
特許番号
US04486588

関連ノート

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