Epichlorohydrin → 1-(Diphenylmethyl)-3-(2-oxiranylmethoxy)azetidine

HRID 2107531Notes

Reaction equation

HRID 2107531 reaction equation
[C:1]1([CH:7]([N:14]2[CH2:17][CH:16]([OH:18])[CH2:15]2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:19]([CH:21]1[O:23][CH2:22]1)Cl>CS(C)=O.[OH-].[Na+]>[C:1]1([CH:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:14]2[CH2:17][CH:16]([O:18][CH2:19][CH:21]3[O:23][CH2:22]3)[CH2:15]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 2

HCID 7835EpichlorohydrinHCID 3304481-(Diphenylmethyl)azetidin-3-ol

Product 1

HCID 151657101-(Diphenylmethyl)-3-(2-oxiranylmethoxy)azetidine

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 14798Sodium HydroxideSolvent

Procedure

37.5 g of diphenylmethylazetidin-3-ol are dissolved at room temperature in a mixture of 250 ml of dimethyl sulphoxide and 150 ml of 5% strength sodium hydroxide solution, 65 ml of epichlorohydrin are added and the mixture is allowed to stand for 3 days at room temperature. The reaction mixture is extracted using 300 ml of methylene chloride, and the organic phase is dried over sodium sulphate and evaporated. The crude product is distilled in vacuo.

Workup

  1. additionare added
  2. extractionThe reaction mixture is extracted
  3. dry with materialthe organic phase is dried over sodium sulphate
  4. customevaporated
  5. distillationThe crude product is distilled in vacuo

Sources & evidence

ORD record
ord-81126fe39c464a82a09e9223c93c7b51
Source dataset
uspto-grants-1990_06
Patent number
US04935414

Reaction notes

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