Diethyl Ether → 2-(5-Bromopentyl)oxirane

HRID 420841Notes

Reaction equation

HRID 420841 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH:7]=[CH2:8].ClC1C=CC=C(C(OO)=[O:17])C=1.C(OCC)C.S([O-])([O-])(=O)=S.[Na+].[Na+]>C(Cl)(Cl)Cl>[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH:7]1[CH2:8][O:17]1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 24477Sodium ThiosulfateHCID 70297m-Chloroperbenzoic acidHCID 5244507-Bromo-1-heptene

Product 1

HCID 142253782-(5-Bromopentyl)oxiraneYield 94.8%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

7-Bromo-1-heptene (5.10 g) was dissolved in chloroform (29 ml), the solution was added with m-chloroperbenzoic acid (6.21 g) under ice cooling, and the mixture was stirred at room temperature for 3 hours. The reaction mixture was added with diethyl ether and saturated aqueous sodium thiosulfate, the layers were separated, and the organic layer was washed with saturated aqueous sodium hydrogencarbonate, then dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under ordinary pressure to obtain the title compound (5.27 g).

Workup

  1. customthe layers were separated
  2. washthe organic layer was washed with saturated aqueous sodium hydrogencarbonate
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated under ordinary pressure

Sources & evidence

ORD record
ord-0681951f2ced40f491ea062d87d9dc12
Source dataset
uspto-grants-2012_01
Patent number
US08097708B2

Reaction notes

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