Triphenylphosphine → 4-(2-chloroethyl)-1-methyl-4,5,6,7-tetrahydro-1H-indole

HRID 447748ノート

反応式

HRID 447748 の反応式
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH3:20][N:21]1[C:29]2[CH2:28][CH2:27][CH2:26][CH:25]([CH2:30][CH2:31]O)[C:24]=2[CH:23]=[CH:22]1.C(Cl)(Cl)(Cl)[Cl:34].C(#N)C>>[Cl:34][CH2:31][CH2:30][CH:25]1[CH2:26][CH2:27][CH2:28][C:29]2[N:21]([CH3:20])[CH:22]=[CH:23][C:24]1=2

参加物

4

反応物 3

HCID 11776TriphenylphosphineHCID 18669661Acetonitrile tetrachloromethaneHCID 578144052-(1-methyl-4,5,6,7-tetrahydro-1H-indol-4-yl)ethanol

生成物 1

HCID 690791294-(2-chloroethyl)-1-methyl-4,5,6,7-tetrahydro-1H-indole収率 43%

実験手順

Triphenylphosphine (2.46 g, 9.38 mmol) is added to a solution of 2-(1-methyl-4,5,6,7-tetrahydro-1H-indol-4-yl)ethanol (1.68 g, 9.38 mmol) in CCl4/Acetonitrile 1:1 (20 mL) at room temperature and the mixture is maintained under stirring for 3 hours monitoring the reaction by TLC. The solution is concentrated to half the volume at reduced pressure, CH2Cl2 is added and washed with water. The organic phase is separated and evaporated to dryness. The crude is treated with diethyl ether and the precipitated is filtered. The diethyl ether is evaporated at reduced pressure, and the resulting crude is purified by column chromatography, giving 4-(2-chloroethyl)-1-methyl-4,5,6,7-tetrahydro-1H-indole (0.8 g, 4.05 mmol, 43%, oil). (ESI-MS m/z 198 (M+H)+.

後処理

  1. temperaturethe mixture is maintained
  2. customthe reaction by TLC
  3. concentrationThe solution is concentrated to half the volume at reduced pressure, CH2Cl2
  4. additionis added
  5. washwashed with water
  6. customThe organic phase is separated
  7. customevaporated to dryness
  8. additionThe crude is treated with diethyl ether
  9. filtrationthe precipitated is filtered
  10. customThe diethyl ether is evaporated at reduced pressure
  11. customthe resulting crude is purified by column chromatography

出典と根拠

ORDレコード
ord-f354015d5b914b869b6f71e3104e19bd
出典データセット
uspto-grants-2013_07
特許番号
US08481567B2

反応ノート

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