Water → Methyl 2,2-dimethylpent-4-enoate

HRID 550544Notes

Reaction equation

HRID 550544 reaction equation
[Li].[C:2]([O:7][CH3:8])(=[O:6])[CH:3]([CH3:5])[CH3:4].[CH2:9](Br)[CH:10]=C.O.[CH2:14]1COCC1>>[CH3:4][C:3]([CH3:14])([CH2:5][CH:9]=[CH2:10])[C:2]([O:7][CH3:8])=[O:6]

Participants

6

Conditions

Temperature
-78 °C

Procedure

To a solution of diisopropilamide (7.6 ml) in THF (12 ml) was added drop by drop n-butil lithium (2.5M in hexane, 21.6 ml) at −78° C. After stirring the reaction mixture at −78° C. for 30 minutes, a solution of methyl isobutyrate (5 g) in THF (12 ml) was added in 10 minutes and the mixture stirred at −78° C. for 1 h. A solution of allyl bromide (4.7 ml) in THF (12 ml) was dropped into the mixture reaction and it was stirred at −78° C. for 1 h. After adding some drop of water, volatiles were evaporated in vacuo, the crude dissolved in ethyl acetate, washed with water and dried over Na2SO4. After filtration volatiles were evaporated in vacuo to give 1.8 g of the title compound as a yellow pale liquid, which was used without further purification.

Workup

  1. stirringthe mixture stirred at −78° C. for 1 h
  2. stirringwas stirred at −78° C. for 1 h
  3. customwere evaporated in vacuo
  4. dissolutionthe crude dissolved in ethyl acetate
  5. washwashed with water
  6. dry with materialdried over Na2SO4
  7. filtrationAfter filtration volatiles
  8. customwere evaporated in vacuo

Sources & evidence

ORD record
ord-3bb9db4d3aa947419641a9791c5c7472
Source dataset
uspto-grants-2011_05
Patent number
US07947683B2

Reaction notes

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