HCID 21461387, compound → HCID 15788050, compound

HRID 1941519Notes

Reaction equation

HRID 1941519 reaction equation
Br[CH2:2][CH:3]1[O:12][CH2:11][CH:10]2[CH:6]([O:7][C:8]([CH3:14])([CH3:13])[O:9]2)[CH2:5][O:4]1>O.C1COCC1>[CH2:2]=[C:3]1[O:4][CH2:5][CH:6]2[CH:10]([O:9][C:8]([CH3:14])([CH3:13])[O:7]2)[CH2:11][O:12]1

Participants

4

Reactant 1

HCID 21461387HCID 21461387, compound

Product 1

HCID 15788050HCID 15788050, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

0.943 mol (105.8 g) of potassium tert.butylate were dissolved in 800 ml of water-free THF. A solution of 865 mmol (231 g) of 4-bromomethyl-9,9-dimethyl-3,5,8,10-tetraoxabicyclo[5.3.0]decane in 800 ml of THF were added dropwise within 90 minutes with stirring and the mixture was subsequently heated for 6 h under reflux. The resulting KBr was filtered and the THF was subsequently distilled under a filter pump vacuum. The dark brown residue underwent fractional distillation under vacuum. 111.2 g of colourless clear 4-methylene-9,9-dimethyl-3,5,8,10-tetraoxabicyclo[5.3.0]decane (yield 70%) go over at between 45° and 49° C. (0.2 mbar).

Workup

  1. temperaturethe mixture was subsequently heated for 6 h
  2. temperatureunder reflux
  3. filtrationThe resulting KBr was filtered
  4. distillationthe THF was subsequently distilled under a filter pump vacuum
  5. distillationThe dark brown residue underwent fractional distillation under vacuum

Sources & evidence

ORD record
ord-5fe6c9ad666e449bbd93035e938e3480
Source dataset
uspto-grants-1997_12
Patent number
US05703249

Reaction notes

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