Dimethylformamide → 2,6-Dichloro-4-morpholin-4-YL-benzaldehyde

HRID 1514949Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1514949
[Cl:1][C:2]1[CH:3]=[C:4]([N:9]2[CH2:14][CH2:13][O:12][CH2:11][CH2:10]2)[CH:5]=[C:6]([Cl:8])[CH:7]=1.[Li]C(CC)C.CN([CH:23]=[O:24])C>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]([N:9]2[CH2:14][CH2:13][O:12][CH2:11][CH2:10]2)[CH:5]=[C:6]([Cl:8])[C:7]=1[CH:23]=[O:24]

Komponenten

5

Edukt 3

HCID 6228DimethylformamideHCID 669665754-(3,5-Dichlorophenyl)morpholineHCID 178418400CID 53628100

Produkt 1

HCID 71486052,6-Dichloro-4-morpholin-4-YL-benzaldehyde

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of to a solution of 4-(3,5-dichlorophenyl)-morpholine (1.60 g, 6.93 mmol) in dry THF (20 mL) under N2 at −78° C. was added dropwise sec-BuLi (1.4M in cyclohexane, 5.44 mL). The solution was allow to stir for 30 min then DMF (2.68 mL, 34.7 mmol) was slowly added to the. Upon disappearance of the starting material by TLC, the reaction was warmed to 0° C. then was quench by addition of H2O (15 mL). The mixture was extracted with EtOAc (150 mL), the organic phase was dried over Na2SO4 and the solvent was evaporate under reduced pressure. The resulting solid was triturated with Et2O to yield 2,6-dichloro-4-morpholin-4-yl-benzaldehyde as an off white solid. 1H NMR (400 MHz, Acetonitrile-d3): δ 10.44 (s, 1H), 7.06 (s, 2H), 3.85-3.93 (m, 4H), 3.46-3.54 (m, 4H). MS (m/z) 260.0 (M+1).

Aufarbeitung

  1. customthen was quench by addition of H2O (15 mL)
  2. extractionThe mixture was extracted with EtOAc (150 mL)
  3. dry with materialthe organic phase was dried over Na2SO4
  4. customthe solvent was evaporate under reduced pressure
  5. customThe resulting solid was triturated with Et2O

Quellen und Nachweise

ORD-Eintrag
ord-6881c0f6e7c147ac92d4af0496a28c86
Quelldatensatz
uspto-grants-2012_07
Patentnummer
US08222248B2

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