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

HRID 720384

Reaction equation

HRID 720384 reaction equation
[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

Participants

5

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 8028TetrahydrofuranSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-246cd350bf024271a337893067ba15ef
Source dataset
uspto-grants-2006_11
Patent number
US07135479B2

Linked notes

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