Acetic Acid → HCID 22144983, Verbindung

HRID 1825037

Reaktionsgleichung

Reaktionsgleichung von HRID 1825037
[CH:1]([C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[CH:6]=O)=[CH2:2].[NH:11]1[CH2:16][CH2:15][O:14][CH2:13][CH2:12]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C>ClCCl>[CH:1]([C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[CH2:6][N:11]1[CH2:16][CH2:15][O:14][CH2:13][CH2:12]1)=[CH2:2]

Komponenten

6

Edukt 4

HCID 176Acetic AcidHCID 8083MorpholineHCID 393903-VinylbenzaldehydeHCID 5049666Sodium triacetoxyborohydride

Produkt 1

HCID 22144983HCID 22144983, VerbindungAusbeute 93,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To the solution of 3-vinyl benzaldehyde (5 g, 38 mmol) and morpholine (3.0 mL, 52 mmol) in dichloromethane (126 ml) was added sodium triacetoxyborohydride (19.2 g, 92 mmol) in portion at 0° C. followed by acetic acid (2.3 mL, 40 mmol). After the addition, reaction mixture was raised to room temperature and stirred at room temperature overnight. The reaction mixture was diluted with dichloromethane washed with 1N NaOH and extracted with dichloromethane 3 times. The combined organic layer was dried over magnesium sulfate and concentrated under vacuum to give the title compound as pale yellow oil (7.2 g, 93% yield)

Aufarbeitung

  1. additionAfter the addition, reaction mixture
  2. washwashed with 1N NaOH
  3. extractionextracted with dichloromethane 3 times
  4. dry with materialThe combined organic layer was dried over magnesium sulfate
  5. concentrationconcentrated under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-ee017e977b1549cc907d6ae55a2fa0d4
Quelldatensatz
uspto-grants-2006_05
Patentnummer
US07045551B2

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