Potassium Carbonate → Ethyl 2-[2-(t-butyloxy)-2-oxo-ethoxy]-5-formylbenzoate

HRID 259774

Reaktionsgleichung

Reaktionsgleichung von HRID 259774
[CH:1]([C:3]1[CH:4]=[CH:5][C:6]([OH:14])=[C:7]([CH:13]=1)[C:8]([O:10][CH2:11][CH3:12])=[O:9])=[O:2].Br[CH2:16][C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[C:20]([O:19][C:17](=[O:18])[CH2:16][O:14][C:6]1[CH:5]=[CH:4][C:3]([CH:1]=[O:2])=[CH:13][C:7]=1[C:8]([O:10][CH2:11][CH3:12])=[O:9])([CH3:23])([CH3:22])[CH3:21]

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 79177tert-Butyl bromoacetateHCID 18930679Ethyl 5-formyl-2-hydroxybenzoate

Produkt 1

HCID 18930723Ethyl 2-[2-(t-butyloxy)-2-oxo-ethoxy]-5-formylbenzoateAusbeute 97,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Phenol 2c (1.0 g, 5.2 mmol), t-butyl bromoacetate (0.84 mL, 5.2 mmol), and potassium carbonate (0.79 g, 5.7 mmol) were heated at 65° C. in DMF (8 mL) overnight. After solvent removal, the mixture was diluted with EtOAc and extracted with water (3×), then brine. Drying (MgSO4) and removal of solvent gave a clear yellow oil (1.56 g). 1H-NMR(300 MHz, CDCl3): 9.93 (s, 1H), 8.35 (d, 1H, J=2 Hz), 7.99 (dd, 1H, J=9,2 Hz), 6.95 (d, 1H, J=9 Hz), 4.71 (s, 2H), 4.41 (q, 2H, J=7 Hz), 1.48 (t, 3H, J=7 Hz). Anal. Calc'd for C16H20O6 : C, 62.33; H, 6.54; Found: C, 62.05; H, 6.58.

Aufarbeitung

  1. customAfter solvent removal
  2. additionthe mixture was diluted with EtOAc
  3. extractionextracted with water (3×)
  4. customDrying
  5. custom(MgSO4) and removal of solvent

Quellen und Nachweise

ORD-Eintrag
ord-aac7ab95d27c41d1a38bb201c3bb4d7a
Quelldatensatz
uspto-grants-1996_06
Patentnummer
US05523302

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