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

HRID 1153842

반응식

HRID 1153842 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 1140Toluene용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-e52eceddde834449b16106a075d0035c
출처 데이터셋
uspto-grants-1984_12
특허 번호
US04486588

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