Phosphorus oxychloride → HCID 23124897、化合物

HRID 644104ノート

反応式

HRID 644104 の反応式
FC1C=CC(C2C3C(=CC=CC=3)N(C(C)C)C=2)=CC=1.P(Cl)(Cl)(Cl)=O.CO/C=C/C#N.C(=O)([O-])O.[Na+].[F:36][C:37]1[CH:42]=[CH:41][C:40]([C:43]2[C:51]3[C:46](=[CH:47][CH:48]=[CH:49][CH:50]=3)[N:45]([CH:52]([CH3:54])[CH3:53])[C:44]=2[CH:55]=[CH:56][C:57]#[N:58])=[CH:39][CH:38]=1>ClCCl>[F:36][C:37]1[CH:42]=[CH:41][C:40]([C:43]2[C:51]3[C:46](=[CH:47][CH:48]=[CH:49][CH:50]=3)[N:45]([CH:52]([CH3:53])[CH3:54])[C:44]=2/[CH:55]=[CH:56]/[C:57]#[N:58])=[CH:39][CH:38]=1

参加物

7

反応物 5

HCID 24813Phosphorus oxychlorideHCID 516892Sodium BicarbonateHCID 7362293-(4-Fluorophenyl)-1-(1-methylethyl)-1H-indoleHCID 53247133-MethoxyacrylonitrileHCID 67196878HCID 67196878、化合物

生成物 1

HCID 23124897HCID 23124897、化合物収率 45%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

Into a solution prepared by dissolving 0.63 g of 3-(4-fluorophenyl)-1-isopropyl-1H-indole in 3 mL of dichloromethane was added dropwise 0.77 g of phosphorus oxychloride at an inner temperature of 0 to 10° C., then, 0.92 g of trans-3-methoxyacrylonitrile was added dropwise. Then, the mixture was stirred overnight at room temperature to cause a reaction, further, the mixture was reacted for 6 hours at the reflux temperature. After completion of the reaction, the reaction liquid was added into 100 mL of 5 wt % aqueous sodium hydrogen carbonate, and extracted with ethyl acetate three times. The resulting organic layers were combined and washed with water, then, dried with anhydrous magnesium sulfate. The magnesium sulfate was filtrated off, and the resulting filtrate was concentrated to obtain a concentrated residue containing 3-[3-(4-fluorophenyl)-1-isopropyl-1H-indol-2-yl]acrylonitrile (trans-cis isomer mixture containing mainly trans isomer). The resulting concentrated residue was purified by silica gel column chromatography (developing liquid: n-heptane/ethyl acetate: 10/1 to 5/1) to obtain 0.34 g of trans-3-[3-(4-fluorophenyl)-1-isopropyl-1H-indol-2-yl]acrylonitrile (yellow solid). Yield: 45%

後処理

  1. customInto a solution prepared
  2. customa reaction
  3. customfurther, the mixture was reacted for 6 hours at the reflux temperature
  4. customAfter completion of the reaction
  5. customthe reaction liquid
  6. extractionextracted with ethyl acetate three times
  7. washwashed with water
  8. dry with materialdried with anhydrous magnesium sulfate
  9. filtrationThe magnesium sulfate was filtrated off
  10. concentrationthe resulting filtrate was concentrated
  11. customto obtain a concentrated residue
  12. additioncontaining mainly trans isomer)
  13. customThe resulting concentrated residue was purified by silica gel column chromatography (developing liquid: n-heptane/ethyl acetate: 10/1 to 5/1)

出典と根拠

ORDレコード
ord-82f3d86290f64b56b5e2170555f0f2bd
出典データセット
uspto-grants-2010_04
特許番号
US07700642B2

反応ノート

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