2-Methoxyethanol → Methoxyethoxy-(3e)-1,3-pentadiene

Under a nitrogen atmosphere, to a stirred solution of sodium (0.53 g, 23 mmol) in 2-methoxyethanol (50 mL) at room temperature was added 5-bromo-(3E)-1,3-pentadiene (3.38 g, 23 mmol). The mixture was stirred overnight and then refluxed for three more hours. Excess 2-methoxyethanol was removed by distillation. Water was added to the cooled reaction mixture, which was then extracted with diethyl ether. The diethyl ether solution was dried over MgSO4, then stripped off at reduced pressure. Distillation at 87-88° C., 31 mmHg (water aspirator) yielded 2.46 g (75%) of the desired compound.

1. temperaturerefluxed for three more hours
2. customExcess 2-methoxyethanol was removed by distillation
3. additionWater was added to the cooled reaction mixture, which
4. extractionwas then extracted with diethyl ether
5. dry with materialThe diethyl ether solution was dried over MgSO4
6. distillationDistillation at 87-88° C.

ORD record

ord-6e059a2bf50c41c48ba8f2be35d870b1

Source dataset

uspto-grants-2002_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06462207B1