Triphenylphosphine → 3,5-Diisopropyl-4-(2-morpholin-4-ylethoxy)-benzaldehyde

HRID 24377

Reaktionsgleichung

Reaktionsgleichung von HRID 24377
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH:20]([C:23]1[CH:24]=[C:25]([CH:28]=[C:29]([CH:32]([CH3:34])[CH3:33])[C:30]=1[OH:31])[CH:26]=[O:27])([CH3:22])[CH3:21].O[CH2:36][CH2:37][N:38]1[CH2:43][CH2:42][O:41][CH2:40][CH2:39]1.CCOC(/N=N/C(OCC)=O)=O>O1CCCC1>[CH:20]([C:23]1[CH:24]=[C:25]([CH:28]=[C:29]([CH:32]([CH3:34])[CH3:33])[C:30]=1[O:31][CH2:36][CH2:37][N:38]1[CH2:43][CH2:42][O:41][CH2:40][CH2:39]1)[CH:26]=[O:27])([CH3:22])[CH3:21]

Komponenten

6

Edukt 4

HCID 11776TriphenylphosphineHCID 611632-MorpholinoethanolHCID 827124-Hydroxy-3,5-bis(isopropyl)benzaldehydeHCID 5462977Diethyl azodicarboxylate

Produkt 1

HCID 225711303,5-Diisopropyl-4-(2-morpholin-4-ylethoxy)-benzaldehydeAusbeute 14,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Triphenylphosphine (5.14 g, 19.58 mmol) was added to a solution of 3,5-diisopropyl-4-hydroxybenzaldehyde (4 g, 19.58 mmol) in tetrahydrofuran (40 ml) followed by addition of 2-hydroxyethylmorpholine (2.57 g, 19.58 mmol) and then the dropwise addition of diethylazodicarboxylate (3.41 g, 19.58 mmol). The mixture was stirred at room temperature for 12 hours. The reaction was concentrated under reduced pressure and partitioned between 2N hydrochloric acid (200 ml) and ethyl acetate (150 ml). The aqueous layer was extracted with ethyl acetate (2×150ml), basified to pH 9 with solid sodium bicarbonate and extracted with ethyl acetate (3×150 ml). The organic layers were combined, dried over magnesium sulfate and concentrated to afford 900 mg (14%) of 3,5-diisopropyl-4-(2-morpholin-4-ylethoxy)-benzaldehyde as a yellowish oil.

Aufarbeitung

  1. concentrationThe reaction was concentrated under reduced pressure
  2. custompartitioned between 2N hydrochloric acid (200 ml) and ethyl acetate (150 ml)
  3. extractionThe aqueous layer was extracted with ethyl acetate (2×150ml)
  4. extractionextracted with ethyl acetate (3×150 ml)
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-0b39b6e87327452e9407713dc876b76e
Quelldatensatz
uspto-grants-2005_02
Patentnummer
US06855730B2

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