Dichloromethane → 3-[(Allyloxy)methyl]-3-ethyloxetane

HRID 2211272Notes

Reaction equation

HRID 2211272 reaction equation
[CH2:1]([C:3]1([CH2:7][OH:8])[CH2:6][O:5][CH2:4]1)[CH3:2].[CH2:9](Br)[CH:10]=[CH2:11].[OH-].[K+].ClCCl>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.O>[CH2:1]([C:3]1([CH2:7][O:8][CH2:11][CH:10]=[CH2:9])[CH2:6][O:5][CH2:4]1)[CH3:2]

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 7841Allyl bromideHCID 14797Potassium HydroxideHCID 76444Oxt-101

Product 1

HCID 152503583-[(Allyloxy)methyl]-3-ethyloxetaneYield 92%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 23.2 g (0.2 mol) of 3-ethyl-3-hydroxymethyloxetane in 48.4 g (0.4 mol) of allylbromide and 50 g of a 50 wt % aqueous solution of potassium hydroxide in a 300 mL round bottom flask equipped with a magnetic stirrer was added 1.0 g of tetra-n-butylammonium bromide with vigorous stirring at 0° C. After 24 hrs, 100 mL of dichlorometane and 100 mL of water were added to the reaction mixture. The organic phase was washed with water twice, dried over magnesium sulfate, filtered and the solvent removed on a rotary evaporator. The residue was purified by distillation under vacuum, giving 28.6 g of 3-ethyl-3-allyloxymethyloxetane (yield 92%, b.p.:55° C. at 1.5 mm Hg).

Workup

  1. washThe organic phase was washed with water twice
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. customthe solvent removed on a rotary evaporator
  5. distillationThe residue was purified by distillation under vacuum

Sources & evidence

ORD record
ord-d1b03f669a6347558c64f69115ec68e5
Source dataset
uspto-grants-1995_10
Patent number
US05463084

Reaction notes

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