2',4'-Dichloroacetophenone → 1-(2,4-Dichlorophenyl)-3-(dimethylamino)prop-2-en-1-one

HRID 968193

反応式

HRID 968193 の反応式
[CH3:1][C:2]([C:4]1[CH:9]=[CH:8][C:7]([Cl:10])=[CH:6][C:5]=1[Cl:11])=[O:3].C(O[CH:15](OCC)[N:16]([CH3:18])[CH3:17])C>>[Cl:11][C:5]1[CH:6]=[C:7]([Cl:10])[CH:8]=[CH:9][C:4]=1[C:2]([CH:1]=[CH:15][N:16]([CH3:18])[CH3:17])=[O:3]

参加物

3

反応物 2

HCID 166932',4'-DichloroacetophenoneHCID 70913Dimethylformamide diethylacetal

生成物 1

HCID 7300441-(2,4-Dichlorophenyl)-3-(dimethylamino)prop-2-en-1-one

実験手順

Part D. A mixture of 2,4-dichloroacetophenone (10.0 g, 52.9 mmol) and dimethylformamide diethyl acetal (10.0 mL, 58.3 mmol) was heated to reflux for 12 hours, then cooled and evaporated under high vacuum. The residual oil was separated by column chromatography (silica gel, 1:1 ethyl acetate-hexane) to afford the product, 1-(2,4-dichlorobenzoyl)-2-(N,N-dimethylamino)ethene, as a viscous oil (12.11 g, 49.6 mmol, 94%). TLC RF 0.05 (20:80 ethyl acetate-hexane). Spectral data: 1H NMR (300 MHz, CDCl3): δ 7.40 (1H, d, J=2.2 Hz), 7.38-7.23 (3H, m), 5.33 (1H, d, J=12.4 Hz), 3.11 (3H, br s), 2.89 (3H, br s). MS (NH3—CI): m/e 249 (1), 248 (10), 247 (8), 246 (64), 245 (16), 244 (100).

後処理

  1. temperaturewas heated
  2. temperatureto reflux for 12 hours
  3. temperaturecooled
  4. customevaporated under high vacuum
  5. customThe residual oil was separated by column chromatography (silica gel, 1:1 ethyl acetate-hexane)

出典と根拠

ORDレコード
ord-6dbf03f698434921a432bb448ff0233b
出典データセット
uspto-grants-2005_10
特許番号
US06958341B2

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