Dimethylformamide → Methyl 4-[4-(5,8-dimethylnaphthalene-2-yl)-4-oxo-butanoyl]benzoate

HRID 277173노트

반응식

HRID 277173 반응식
[CH3:1][C:2]1[CH:11]=[CH:10][C:9]([CH3:12])=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([CH:13]=[O:14])=[CH:7]2.[C:15]([C:19]1[CH:28]=[CH:27][C:22]([C:23]([O:25][CH3:26])=[O:24])=[CH:21][CH:20]=1)(=[O:18])[CH:16]=[CH2:17].C(N(CC)CC)C.CN(C)C=O>O>[CH3:1][C:2]1[CH:11]=[CH:10][C:9]([CH3:12])=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([C:13](=[O:14])[CH2:17][CH2:16][C:15]([C:19]1[CH:28]=[CH:27][C:22]([C:23]([O:25][CH3:26])=[O:24])=[CH:21][CH:20]=1)=[O:18])=[CH:7]2

참가 물질

6

반응물 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 10774024Methyl 4-acryloyl-benzoateHCID 144876095,8-Dimethyl-2-naphthaldehyde

생성물 1

HCID 15487489Methyl 4-[4-(5,8-dimethylnaphthalene-2-yl)-4-oxo-butanoyl]benzoate수율 40.3%

시약·촉매·용매 1

HCID 962Water용매

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온도
70 °C

실험 절차

A mixture of 1.0 g of 5,8-dimethyl-2-naphthaldehyde, 1.2 g of methyl 4-acryloyl-benzoate, 0.28 g of 3-benzyl-5-(2-hydroxymethyl)-4-methylthiazolium chloride, 0.88 ml triethylamine and 20 ml N,N-dimethylformamide was heated under stirring at 70° C. for 3 hours. After the reaction solution was left standing for cooling to room temperature, water was added thereto, and the reaction solution was extracted with ethyl acetate (20 ml×3). The organic layers were combined, washed with brine, dried over anhydrous magnesium sulfate and filtered. Then, the filtrate was concentrated and the resulting crude crystals were washed with a mixed solvent of n-hexane and ethyl acetate to give 0.82 g of the title compound as colorless crystals.

후처리

  1. temperaturewas heated
  2. waitAfter the reaction solution was left
  3. temperaturefor cooling to room temperature
  4. extractionthe reaction solution was extracted with ethyl acetate (20 ml×3)
  5. washwashed with brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. concentrationThen, the filtrate was concentrated
  9. washthe resulting crude crystals were washed with a mixed solvent of n-hexane and ethyl acetate

출처 및 근거

ORD 기록
ord-846f97dcc71e43768acfd60278ef6283
출처 데이터셋
uspto-grants-2002_03
특허 번호
US06355669B1

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