Sodium Bicarbonate → (1-Benzhydryl-azetidin-3-yl)-acetaldehyde

HRID 720384

Reaktionsgleichung

Reaktionsgleichung von HRID 720384
[CH:1]([N:14]1[CH2:17][C:16](=[CH:18]OC)[CH2:15]1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:21](=O)(O)[O-:22].[Na+]>O1CCCC1.Cl>[CH:1]([N:14]1[CH2:17][CH:16]([CH2:18][CH:21]=[O:22])[CH2:15]1)([C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Komponenten

5

Edukt 2

HCID 516892Sodium BicarbonateHCID 218920531-Benzhydryl-3-(methoxymethylene)azetidine

Produkt 1

HCID 58739272(1-Benzhydryl-azetidin-3-yl)-acetaldehyde

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 313Hydrochloric AcidLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of 1-benzhydryl-3-methoxymethylene-azetidine (0.19 g, 0.88 mmol) in tetrahydrofuran (20 mL) and 1N hydrogen chloride (10 mL) was refluxed overnight. The mixture was neutralized with saturated sodium bicarbonate and extracted with methylene chloride (3×50 mL). The combined organic extracts were washed with water (3×50 mL), dried over anhydrous sodium sulfate, filtered and concentrated in vacuum to afford 0.17 g of the title compound as a light yellow oil. 1H NMR (400 MHz, DMSO-D6): δ 3.2 (br, 4H), 4.42 (s, 1H), 7.13–7.18 (m, 2H), 7.23–7.27 (m, 4H), 7.37–7.40 (m, 4H).

Aufarbeitung

  1. extractionextracted with methylene chloride (3×50 mL)
  2. washThe combined organic extracts were washed with water (3×50 mL)
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuum

Quellen und Nachweise

ORD-Eintrag
ord-246cd350bf024271a337893067ba15ef
Quelldatensatz
uspto-grants-2006_11
Patentnummer
US07135479B2

Verknüpfte Notizen

Wird geladen…