Chloride → 3-Methyl-3-{[(prop-2-en-1-yl)oxy]methyl}oxetane

HRID 915538Notes

Reaction equation

HRID 915538 reaction equation
[CH3:1][CH:2]1[CH2:5][O:4][CH:3]1CO.[H-].[Na+].[H][H].[Cl-]>C1COCC1>[CH2:3]([O:4][CH2:5][C:2]1([CH3:1])[CH2:3][O:4][CH2:5]1)[CH:2]=[CH2:1]

Participants

6

Procedure

The 3-methyl oxetanemethanol (1 mole) is dissolved in THF (500 mL) and fed into 60% sodium hydride dispersion (1.1 mole) in THF (500 mL) at 0° C. Following evolution of hydrogen gas the ally chloride (1.1 mole) is added to the reaction at room temperature. The reaction is aged for 2-4 hrs. The reaction is quenched when GC analysis indicates less than 10% starting alcohol is present. The reaction mass is washed with 10% aqueous sodium chloride solution. The crude reaction mass is purified by fractional distillation affording 114 g of 3-allyloxymethyl-3-methyl-oxetane.

Workup

  1. additionis added to the reaction at room temperature
  2. customThe reaction is quenched when GC analysis
  3. washThe reaction mass is washed with 10% aqueous sodium chloride solution
  4. customThe crude reaction mass
  5. distillationis purified by fractional distillation

Sources & evidence

ORD record
ord-59fb78b48a2d472a91cef7584329531e
Source dataset
uspto-grants-2007_09
Patent number
US07265231B2

Reaction notes

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