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

HRID 277173ノート

反応式

HRID 277173 の反応式
[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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
70 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-846f97dcc71e43768acfd60278ef6283
出典データセット
uspto-grants-2002_03
特許番号
US06355669B1

反応ノート

読み込み中…