Dimethylformamide → 2-Chlorocyclohex-1-enecarbaldehyde

HRID 1473243ノート

反応式

HRID 1473243 の反応式
P(Cl)(Cl)([Cl:3])=O.CN(C)[CH:8]=[O:9].[C:11]1(=O)[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1>>[Cl:3][C:11]1[CH2:16][CH2:15][CH2:14][CH2:13][C:12]=1[CH:8]=[O:9]

参加物

4

反応物 3

HCID 6228DimethylformamideHCID 7967CyclohexanoneHCID 24813Phosphorus oxychloride

生成物 1

HCID 118048922-Chlorocyclohex-1-enecarbaldehyde収率 217.4%

実験手順

Phosphoryl trichloride (125 g, 815 mmol) was added dropwise into a flame-dried bottom flask containing N,N-dimethylformamide (74.5 g, 1019 mmol) at 0° C. with stirring. After addition, the mixture was warmed to ambient temperature for 30 min, and re-cooled to 0° C. before the dropwise addition of cyclohexanone (50 g, 509 mmol). The mixture was warmed to room temperature for 12 h. The reaction was poured over ice and quenched with NaHCO3. Once neutralized, the mixture was extracted with ethyl acetate (100 mL×3) and washed with water and brine. The organic phase was dried, filtered, and concentrated to afford the product (160 g, 87% yield). 1H NMR: (CDCl3, 400 MHz) δ 1.74˜1.75 (m, 2H), 1.76˜1.78 (m, 2H), 2.24˜2.27 (m, 2H), 2.53˜2.59 (m, 2H), 7.25 (s, 1H).

後処理

  1. additionAfter addition
  2. temperatureThe mixture was warmed to room temperature for 12 h
  3. additionThe reaction was poured over ice
  4. customquenched with NaHCO3
  5. extractionthe mixture was extracted with ethyl acetate (100 mL×3)
  6. washwashed with water and brine
  7. customThe organic phase was dried
  8. filtrationfiltered
  9. concentrationconcentrated

出典と根拠

ORDレコード
ord-fdaa50e9f14e472f8cf7bd47ad71bf65
出典データセット
uspto-grants-2015_04
特許番号
US09012642B2

反応ノート

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