2-Bromopropane → 3-(1-Admantyl)-4-isopropoxybenzaldehyde

HRID 710448Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 710448
[C:1]12([C:11]3[CH:12]=[C:13]([CH:16]=[CH:17][C:18]=3[OH:19])[CH:14]=[O:15])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.C([O-])([O-])=O.[K+].[K+].Br[CH:27]([CH3:29])[CH3:28]>CN(C=O)C.CCOC(C)=O>[C:1]12([C:11]3[CH:12]=[C:13]([CH:16]=[CH:17][C:18]=3[O:19][CH:27]([CH3:29])[CH3:28])[CH:14]=[O:15])[CH2:2][CH:3]3[CH2:9][CH:7]([CH2:6][CH:5]([CH2:4]3)[CH2:10]1)[CH2:8]2

Komponenten

6

Edukt 3

HCID 63582-BromopropaneHCID 11430Potassium CarbonateHCID 34078923-(1-Admantyl)-4-hydroxybenzaldehyde

Produkt 1

HCID 871266563-(1-Admantyl)-4-isopropoxybenzaldehydeAusbeute 86 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a stirred suspension of 3-(1-admantyl)-4-hydroxybenzaldehyde (0.5 g, 1.95 mmol) and K2CO3 (0.276 g, 2 mmol) in anhydrous DMF (5 ml) was added 2-bromopropane (1 ml) and the mixture was reflux for 2 h. The reaction mixture was brought to room temperature and diluted to 50 ml with EtOAc and washed with H2O. The organic layer was separated, dried over MgSO4 and filtered. The filtrate was evaporated to dryness and the residue was crystallized from MeOH to give the title compound (0.25 g, 86%), as a colourless solid. 1H-NMR (CDCl3) 1.42 (d, 6H, J=6 Hz); 1.76 (broad s, 6H); 2.07 (broad s, 3H); 2.12 (s, 6H); 4.69-4.78 (m, 1H); 6.91 (d, 1H, J=8.44 Hz); 7.66 (dd, 1H, J=2.13, 8.45 Hz); 7.76 (d, 1H, J=2.11 Hz); 9.84 (s, 1H).

Aufarbeitung

  1. temperaturethe mixture was reflux for 2 h
  2. customwas brought to room temperature
  3. washwashed with H2O
  4. customThe organic layer was separated
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customThe filtrate was evaporated to dryness
  8. customthe residue was crystallized from MeOH

Quellen und Nachweise

ORD-Eintrag
ord-6ee090b971774480b882f9a9aa67a059
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09181182B2

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