Phosphoric Acid → 1-(Diphenylmethyl)azetidine-3-carbaldehyde

HRID 2050182Notes

Reaction equation

HRID 2050182 reaction equation
[C:1]1([CH:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[N:8]2[CH2:11][CH:10]([CH2:12][OH:13])[CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.P(=O)(O)(O)O.C1(N=C=NC2CCCCC2)CCCCC1>CS(C)=O>[C:1]1([CH:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[N:8]2[CH2:11][CH:10]([CH:12]=[O:13])[CH2:9]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 1004Phosphoric AcidHCID 10868DicyclohexylcarbodiimideHCID 2758715(1-Benzhydrylazetidin-3-yl)methanol

Product 1

HCID 203422541-(Diphenylmethyl)azetidine-3-carbaldehydeYield 56.9%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of 2.27 g (8.96 mmoles) of 1-diphenylmethyl-3-hydroxymethylazetidine in 30 ml of dimethylsulfoxide are added 586 mg (0.67 equivalent) of phosphoric acid and 4.25 g (2.3 equivalents) of dicyclohexylcarbodiimide, and the mixture is stirred at room temperature overnight. The insoluble materials are filtered off, and the filtrate is alkalified with an aqueous sodium carbonate solution and extracted with ethyl acetate. The extract is reextracted three times with 14.9% aqueous sodium hydrogensulfite solution. The extract is alkalified with 10% aqueous sodium hydroxide solution and extracted with methylene chloride. The extract is dried and evaporated to yield 1.281 g of crude light yellow syrupy 1-diphenylmethyl-3-formylazetidine in 56.9% yield.

Workup

  1. filtrationThe insoluble materials are filtered off
  2. extractionextracted with ethyl acetate
  3. extractionextracted with methylene chloride
  4. customThe extract is dried
  5. customevaporated

Sources & evidence

ORD record
ord-46d807b46f4f4e92915862e77604ab1e
Source dataset
uspto-grants-1980_04
Patent number
US04200628

Reaction notes

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