Allyl bromide → Ethyl 2-(allyloxy)propanoate

HRID 1368699Notes

Reaction equation

HRID 1368699 reaction equation
[C:1]([O:6][CH2:7][CH3:8])(=[O:5])[C@H:2]([CH3:4])[OH:3].[H-].[Na+].[CH2:11](Br)[CH:12]=[CH2:13]>C1COCC1>[CH2:13]([O:3][CH:2]([CH3:4])[C:1]([O:6][CH2:7][CH3:8])=[O:5])[CH:12]=[CH2:11]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 24758Sodium hydrideHCID 92831(L)-ethyl lactate

Product 1

HCID 535120Ethyl 2-(allyloxy)propanoateYield 100.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

23.6 g (0.2 mol) of ethyl (S)-(−)-lactate, dissolved in 100 ml of THF, are added to a suspension of 8.0 g (0.2 mol) of NaH in 150 ml THF. When the addition is complete, 36.3 g (0.3 mol) of allyl bromide, dissolved in 10 ml of THF, are added dropwise. Some KI is then added and the mixture is refluxed for 16 h. The mixture is then cooled and the reaction is quenched with 100 ml of 2N HCl. The aqueous phase is extracted twice more with Et2O before the combined organic phases are dried over Na2SO4. The mixture is then filtered and the filtrate is evaporated to dryness on a rotary evaporator, giving 31.7 g of crude product (GC purity 89.0%), which is used in the next reactions without further purification.

Workup

  1. additionWhen the addition
  2. additionare added dropwise
  3. additionSome KI is then added
  4. temperaturethe mixture is refluxed for 16 h
  5. temperatureThe mixture is then cooled
  6. customthe reaction is quenched with 100 ml of 2N HCl
  7. extractionThe aqueous phase is extracted twice more with Et2O before the combined organic phases
  8. dry with materialare dried over Na2SO4
  9. filtrationThe mixture is then filtered
  10. customthe filtrate is evaporated to dryness on a rotary evaporator

Sources & evidence

ORD record
ord-81e83e6cbb164b06855dd0ae91252113
Source dataset
uspto-grants-2003_06
Patent number
US06573391B1

Reaction notes

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