Triphenylphosphine → 4-(2-Chloroethyl)-4,5,6,7-tetrahydrobenzo[b]thiophene

HRID 453720ノート

反応式

HRID 453720 の反応式
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[S:20]1[CH:24]=[CH:23][C:22]2[CH:25]([CH2:29][CH2:30]O)[CH2:26][CH2:27][CH2:28][C:21]1=2.C(Cl)(Cl)(Cl)[Cl:33].C(#N)C>>[Cl:33][CH2:30][CH2:29][CH:25]1[C:22]2[CH:23]=[CH:24][S:20][C:21]=2[CH2:28][CH2:27][CH2:26]1

参加物

4

反応物 3

HCID 11776TriphenylphosphineHCID 107499572-(4,5,6,7-Tetrahydrobenzo[b]thiophen-4-yl)ethanolHCID 18669661Acetonitrile tetrachloromethane

生成物 1

HCID 578554434-(2-Chloroethyl)-4,5,6,7-tetrahydrobenzo[b]thiophene収率 56%

実験手順

Triphenylphosphine (3.94 g, 15 mmol) is added to a solution of 2-(4,5,6,7-tetrahydrobenzo[b]thiophen-4-yl)ethanol (2.74 g, 15 mmol) in Cl4C/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 precipitate is filtered. The diethyl ether is evaporated to dryness, and the resulting crude is purified by column chromatography, giving 4-(2-chloroethyl)-4,5,6,7-tetrahydrobenzo[b]thiophene (1.7 g, 8.4 mmol, 56%, oil). 1H NMR (300 MHz, CDCl3): δ 1.54 (m, 1H), 1.79 (m, 1H), 1.92 (m, 3H), 2.20 (m, 1H), 2.77 (m, 2H), 3.00 (m, 1H), 3.64 (m, 2H), 6.86 (d, J=5.2 Hz, 1H), 7.06 (d, J=5.2 Hz, 1H).

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 precipitate is filtered
  10. customThe diethyl ether is evaporated to dryness
  11. customthe resulting crude is purified by column chromatography

出典と根拠

ORDレコード
ord-70974c7a51ae4384bda1e534df33ff47
出典データセット
uspto-grants-2013_07
特許番号
US08492563B2

反応ノート

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