Allyl bromide → HCID 10630623, compound

HRID 1924367Notes

Reaction equation

HRID 1924367 reaction equation
[OH:1][CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].[H-].[Na+].[CH2:10](Br)[CH:11]=[CH2:12]>CN(C=O)C>[CH2:12]([O:1][CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4])[CH:11]=[CH2:10]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 12184Ethyl GlycolateHCID 24758Sodium hydride

Product 1

HCID 10630623HCID 10630623, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Ethyl hydroxyacetate was added dropwise to a slurry of NaH (1.1 eq) in DMF at 0° C. and the resulting mixture was stirred at RT for 2 h. After cooling to 0° C., allylbromide (1.1 eq) was added dropwise via syringe and the reaction mixture was stirred at RT for 2 h, quenched by careful addition of sat. aq. NH4Cl and partitioned between Et2O and brine. The organic layer was dried (Na2SO4) and concentrated under reduced pressure to give the title compound as pale yellow oil. 1H NMR (300 MHz, CDCl3) δ 5.91 (m, 1H), 5.30 (dd, J 17.2, 1.5, 1H), 5.24 (dd, J 10.6, 0.6, 1H), 4.23 (q, J 2.1, 2H), 4.10 (d, J 5.7, 2H), 4.08 (s, 2H), 1.29 (t, J 7.08, 3H).

Workup

  1. temperatureAfter cooling to 0° C.
  2. stirringthe reaction mixture was stirred at RT for 2 h
  3. customquenched by careful addition of sat. aq. NH4Cl
  4. custompartitioned between Et2O and brine
  5. dry with materialThe organic layer was dried (Na2SO4)
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-4a54c4f516c64660957776f3f8ac66f7
Source dataset
uspto-grants-2012_05
Patent number
US08178520B2

Reaction notes

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