Acetone → 1-Oxa-2-aza-spiro[4.5]dec-2-ene-3-carbaldehyde

HRID 1518151Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1518151
C[O:2][CH:3](OC)[C:4]1[CH2:8][C:7]2([CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]2)[O:6][N:5]=1.CC(C)=O>O>[O:6]1[C:7]2([CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]2)[CH2:8][C:4]([CH:3]=[O:2])=[N:5]1

Komponenten

4

Edukt 2

HCID 180AcetoneHCID 592800713-Dimethoxymethyl-1-oxa-2-aza-spiro[4.5]dec-2-ene

Produkt 1

HCID 592801071-Oxa-2-aza-spiro[4.5]dec-2-ene-3-carbaldehydeAusbeute 54 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

3-Dimethoxymethyl-1-oxa-2-aza-spiro[4.5]dec-2-ene (1.06 g, 4.97 mmol, as prepared in the previous step) was placed in a 50 mL round-bottom flask equipped with a stir bar. Acetone (20 mL), water (0.3 mL), and Amberlyst-15 resin (200 mg) were added. The mixture was stirred at rt for 24 h. The solids were removed by filtration and rinsed with acetone (20 mL), and the solvent was removed under reduced pressure. The residue was purified by column chromatography using a 40-g SiO2 pre-packed column eluting with EtOAc/heptane, 0:1 to 3:2, v/v over 30 min, yielding 451 mg (54%) of the desired compound. 1H-NMR (400 MHz, CDCl3) δ: 9.90 (s, 1H), 2.81 (s, 2H), 1.72-1.87 (m, 4H), 1.58-1.69 (m, 2H), 1.40-1.53 (m, 4H).

Aufarbeitung

  1. customwas placed in a 50 mL round-bottom flask
  2. customequipped with a stir bar
  3. customThe solids were removed by filtration
  4. washrinsed with acetone (20 mL)
  5. customthe solvent was removed under reduced pressure
  6. customThe residue was purified by column chromatography
  7. washeluting with EtOAc/heptane, 0:1 to 3:2, v/v over 30 min

Quellen und Nachweise

ORD-Eintrag
ord-5941587369e64a9eb295a077e11864ac
Quelldatensatz
uspto-grants-2012_07
Patentnummer
US08232409B2

Notizen zur Reaktion

Wird geladen…