Tetrahydrofuran → 2-(3-(Benzyloxy)phenyl)-2-methylpropanal

HRID 1155846Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1155846
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([C:15]([CH3:19])([CH3:18])[C:16]#N)[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].C([Al+]CC(C)C)C(C)C.[O:30]1CCCC1>CCCCCC>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([C:15]([CH3:19])([CH3:18])[CH:16]=[O:30])[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 8028TetrahydrofuranHCID 204968632-(3-(Benzyloxy)phenyl)-2-methylpropanenitrileHCID 21225700Diisobutylaluminumhydride

Produkt 1

HCID 198553592-(3-(Benzyloxy)phenyl)-2-methylpropanalAusbeute 99 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8058HexaneLösungsmittel

Versuchsvorschrift

To a 15° C. solution of 325 g. (1.25 mole) of 2-(3-benzyloxyphenyl)-2-methylpropionitrile in 1.85 liters of tetrahydrofuran is added 1.6 moles of diisobutylaluminum hydride as a 1.3 M solution in hexane (reaction temperature is maintained at 15°-18° C.). The reaction mixture is allowed to warm to room temperature and is stirred 2 hours longer. It is then quenched by addition to a solution of 170 ml. of concentrated sulfuric acid in 670 ml. of water (temperature ≤30° C.). The resultant mixture is allowed to warm to room temperature and is then stirred an additional 2 hours. The organic layer is separated and the aqueous phase extracted once with one liter of ether. The combined organic phase is washed with 500 ml. of water and 500 ml. of saturated sodium chloride, dried over magnesium sulfate and evaporated to yield 315 g. (99%) of the title product.

Aufarbeitung

  1. customTo a 15° C.
  2. customIt is then quenched by addition to a solution of 170 ml
  3. customof water (temperature ≤30° C.)
  4. temperatureto warm to room temperature
  5. stirringis then stirred an additional 2 hours
  6. customThe organic layer is separated
  7. extractionthe aqueous phase extracted once with one liter of ether
  8. washThe combined organic phase is washed with 500 ml
  9. dry with materialof saturated sodium chloride, dried over magnesium sulfate
  10. customevaporated
  11. customto yield 315 g

Quellen und Nachweise

ORD-Eintrag
ord-9a837b4387e1421d95db2bd7d2eb3da7
Quelldatensatz
uspto-grants-1982_06
Patentnummer
US04332942

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