(+)-Styrene oxide → 2-Phenyl-1-propanol, (+-)-

HRID 392933

反応式

HRID 392933 の反応式
[CH3:1][Al](C)C.[CH2:5]1[O:7][C@@H:6]1[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>C1(C)C=CC=CC=1>[C:8]1([C@@H:6]([CH3:1])[CH2:5][OH:7])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

参加物

4

反応物 2

HCID 114705(+)-Styrene oxideHCID 16682925Trimethylaluminum

生成物 1

HCID 1770502-Phenyl-1-propanol, (+-)-収率 92.6%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒2 回

反応条件

温度
-60 °C

実験手順

An oven dried 500.0 mL three necked round bottom flask equipped with a mechanical stirrer, thermometer, addition funnel with a continuous nitrogen blanket is charged with 2.0 M solution of trimethylaluminum (65.6 mL, 131.2 mmol) and toluene (75.0 mL). Reaction solution was then chilled to −60° C. with dry ice/acetone bath. To this solution was then added R-styrene oxide dissolved in 100.0 mL of toluene over a period of 50.0 minutes (reaction is quite exothermic and can be controlled by the rate of addition of substrate). After stirring at this temperature for 60.0 minutes, reaction was brought to room temperature and stirred for 4.0 hours. Reverse quenched reaction at room temperature into a slurry of THF (100.0 mL) and sodium sulfate decahydrate (46.0 g) very cautiously over a period of 90.0 minutes (quenching was quite exothermic with evolution of gas). Filtered the precipitate formed over hyflo, then concentrated filtrate to provide the intermediate title compound, (2R)2-phenylpropan-1-ol, (11.03 g, 92.6%) as an oil; 1H nmr (CDCl3, 300 MHz) δ 1.28-1.29 (d, 3H, J=6.9 Hz), 1.5 (b, 1H), 2.9-3.0 (m, 1H), 3.69-3.70 (d, 2H, J=6.64 Hz), 7.24-7.35 (aromatic); 13C nmr (CDCl3, 300 MHz) δ 18.31, 43.15, 69.40, 127.38, 128.20, 129.26, 144.39.

後処理

  1. dry with materialAn oven dried 500.0 mL three necked round bottom flask
  2. customequipped with a mechanical stirrer
  3. additionthermometer, addition funnel with a continuous nitrogen blanket
  4. customReaction solution
  5. customreaction
  6. additioncan be controlled by the rate of addition of substrate)
  7. customreaction
  8. customwas brought to room temperature
  9. stirringstirred for 4.0 hours
  10. customReverse quenched
  11. customreaction at room temperature into a slurry of THF (100.0 mL) and sodium sulfate decahydrate (46.0 g) very cautiously over a period of 90.0 minutes (
  12. customquenching
  13. filtrationFiltered the precipitate
  14. customformed over hyflo

出典と根拠

ORDレコード
ord-7b277e2877b946b181f967f8a606a82a
出典データセット
uspto-grants-2004_10
特許番号
US06803484B2

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