Allyl bromide → HCID 54055058, compound

HRID 1603945Notes

Reaction equation

HRID 1603945 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH:10]([C:15]([O:17][CH3:18])=[O:16])[C:11]([O:13][CH3:14])=[O:12])=[CH:5][C:4]=1[O:19][CH2:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.[H-].[Na+].Br[CH2:31][CH:32]=[CH2:33]>COCCOC>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]([C:11]([O:13][CH3:14])=[O:12])([CH2:33][CH:32]=[CH2:31])[C:15]([O:17][CH3:18])=[O:16])=[CH:5][C:4]=1[O:19][CH2:20][CH2:21][C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 24758Sodium hydrideHCID 10237251HCID 10237251, compound

Product 1

HCID 54055058HCID 54055058, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

To a solution of the crude methyl 3-[4-methoxy-3-(2-phenylethoxy)phenyl]-2-methoxycarbonylpropionate (7.45 g) in 75 ml of 1,2-dimethoxyethane, 0.80 g of 60% sodium hydride (oily) was added little by little at room temperature under stirring. The resultant solution was stirred further at 40° C. for 1.5 hours. To this solution, 2.66 g of 3-bromo-1-propene was added and stirred at room temperature for 1.5 days. The reaction solution was concentrated under reduced pressure and the residue was dissolved in ethyl acetate. This solution was washed with water, a saturated aqueous solution of sodium hydrogencarbonate and a saturated aqueous solution of NaCl in consecutive order and dried over anhydrous magnesium sulfate. The drying agent was separated by filtration and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=4:1) to obtain 7.76 g of methyl 3-[4-methoxy-3-(2-phenylethoxy) phenyl]-2-methoxycarbonyl-2-(2-propen-1-yl)propionate.

Workup

  1. stirringstirred at room temperature for 1.5 days
  2. concentrationThe reaction solution was concentrated under reduced pressure
  3. dissolutionthe residue was dissolved in ethyl acetate
  4. washThis solution was washed with water
  5. dry with materiala saturated aqueous solution of sodium hydrogencarbonate and a saturated aqueous solution of NaCl in consecutive order and dried over anhydrous magnesium sulfate
  6. customThe drying agent was separated by filtration
  7. concentrationthe filtrate was concentrated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=4:1)

Sources & evidence

ORD record
ord-9daf9174ae8e453593266996d32e3221
Source dataset
uspto-grants-1999_11
Patent number
US05990151

Reaction notes

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