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

HRID 2056370Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2056370
[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, 4 H), 4.42 (s, 1 H), 7.13-7.18 (m, 2H), 7.23-7.27 (m, 4 H), 7.37-7.40 (m, 4 H).

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-e8b7c59d3de54d2299cbf4dddddef2af
Quelldatensatz
uspto-grants-2008_02
Patentnummer
US07335666B2

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