2-(3-Chloropropyl)-1,3-dioxolane → HCID 53647093, compound

HRID 355999Notes

Reaction equation

HRID 355999 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][CH:5]1OCCO1.Cl.[C:11]1([O:17][NH2:18])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>C1COCC1>[C:11]1([O:17][N:18]=[CH:5][CH2:4][CH2:3][CH2:2][Cl:1])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

4

Reactant 2

HCID 5520722-(3-Chloropropyl)-1,3-dioxolaneHCID 6365179O-Phenylhydroxylamine hydrochloride

Product 1

HCID 53647093HCID 53647093, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 2-(3-chloro-propyl)-[1,3]-dioxolane (5.7 g; 0.038 mol), THF (50 ml) and aqueous acid chloride (1/1) was stirred at room temperature for 24 hours. O-phenyl-hydroxylamine hydrochloride (5 g; 0.034 mol) was then added and the resulting mixture was stirred at room temperature for 48 hours. The reaction mixture was concentrated under vacuum. Then the product was extracted with methylene chloride. The organic extract was dried (Mg SO4) and evaporated under vacuum. After purification by Flash Chromatography on silica gel using as eluent hexane/ethyl acetate (95/5), the desired compound was obtained.

Workup

  1. stirringthe resulting mixture was stirred at room temperature for 48 hours
  2. concentrationThe reaction mixture was concentrated under vacuum
  3. extractionThen the product was extracted with methylene chloride
  4. extractionThe organic extract
  5. dry with materialwas dried (Mg SO4)
  6. customevaporated under vacuum
  7. customAfter purification by Flash Chromatography on silica gel using as eluent hexane/ethyl acetate (95/5)

Sources & evidence

ORD record
ord-113df8cd62af48768960ecf8d33604fc
Source dataset
uspto-grants-1998_11
Patent number
US05834493

Reaction notes

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