Triethylamine → 1-(Diphenylmethyl)-2-azetidinecarboxaldehyde

HRID 1702759Notes

Reaction equation

HRID 1702759 reaction equation
Cl.[CH:2]([N:15]1[CH2:18][CH2:17][CH:16]1[CH2:19][OH:20])([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C(N(CC)CC)C>CS(C)=O>[CH:2]([N:15]1[CH2:18][CH2:17][CH:16]1[CH:19]=[O:20])([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 12717144[1-(Diphenylmethyl)azetidin-2-yl]methanol--hydrogen chloride (1/1)

Product 1

HCID 127171451-(Diphenylmethyl)-2-azetidinecarboxaldehyde

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

To a stirred mixture of 9.0 g of 1-benzhydrylazetidine-2-methanol hydrochloride, 26.1 ml of triethylamine and 60 ml of dimethylsulfoxide were added dropwise a solution of 14.9 g pyridine-sulfur trioxide complex in 60 ml of dimethylsulfoxide. The mixture was stirred at room temperature for 30 minutes, after which it was poured into ice water and extracted with ethyl acetate. The extract was washed with water and dried over anhydrous magnesium sulfate, followed by removal of the solvent by distillation. The residue was recrystallized from n-hexane to yield 1-benzhydrylazetidine-2-carbaldehyde as colorless crystals melting at 88°-89° C.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customfollowed by removal of the solvent by distillation
  5. customThe residue was recrystallized from n-hexane

Sources & evidence

ORD record
ord-ae2f7d52bed944d19da01b4b64129f77
Source dataset
uspto-grants-1982_09
Patent number
US04349547

Reaction notes

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