Triethylamine → Ethyl 2-[2,5-difluorobenzoyl]-3-dimethylamino-2-propenoate

HRID 2237364

反応式

HRID 2237364 の反応式
[F:1][C:2]1[CH:10]=[CH:9][C:8]([F:11])=[CH:7][C:3]=1[C:4](Cl)=[O:5].[CH2:12]([O:14][C:15](=[O:21])[CH:16]=[CH:17][N:18]([CH3:20])[CH3:19])[CH3:13].C(N(CC)CC)C>C1(C)C=CC=CC=1>[F:1][C:2]1[CH:10]=[CH:9][C:8]([F:11])=[CH:7][C:3]=1[C:4]([C:16](=[CH:17][N:18]([CH3:20])[CH3:19])[C:15]([O:14][CH2:12][CH3:13])=[O:21])=[O:5]

参加物

5

反応物 3

HCID 8471TriethylamineHCID 121015Ethyl 3-(N,N-dimethylamino)acrylateHCID 5880822,5-Difluorobenzoyl chloride

生成物 1

HCID 68584816Ethyl 2-[2,5-difluorobenzoyl]-3-dimethylamino-2-propenoate収率 11.3%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

反応条件

温度
90 °C

実験手順

A solution of 2,5-difluorobenzoyl chloride (5.26 g, 29.8 mmol) in toluene (100 mL) was treated with ethyl-3-(dimethylamino)-2-propenoate (5.27 g, 36.8 mmol), followed by triethylamine (5.9 mL, 42.5 mmol). The mixture was stirred at 90° C. for 6.5 h then allowed to cool, and the precipitate removed by filtration. The filtrate was concentrated under reduced pressure to give a residue which was purified by flash chromatography (silica gel, 50-100% diethyl ether in petroleum ether [b.p. 40-60° C.]) to give the title compound as a yellow oil (0.95 g); ESMS m/z 284.4 [M+H]+.

後処理

  1. temperatureto cool
  2. customthe precipitate removed by filtration
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. customto give a residue which
  5. customwas purified by flash chromatography (silica gel, 50-100% diethyl ether in petroleum ether [b.p. 40-60° C.])

出典と根拠

ORDレコード
ord-e889998953af434a9fd929934d35e758
出典データセット
uspto-grants-2010_05
特許番号
US07718621B2

関連ノート

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