Allyl bromide → HCID 20340335, compound

HRID 1395136Notes

Reaction equation

HRID 1395136 reaction equation
[C:1]([C:3](=[C:10]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:4]([O:6][CH2:7][CH2:8][OH:9])=[O:5])#[N:2].[H-].[Na+].[CH2:25](Br)[CH:26]=[CH2:27]>>[CH2:27]([O:9][CH2:8][CH2:7][O:6][C:4](=[O:5])[C:3]([C:1]#[N:2])=[C:10]([C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)[CH:26]=[CH2:25]

Participants

4

Reactant 3

HCID 7841Allyl bromideHCID 24758Sodium hydrideHCID 19020936HCID 19020936, compound

Product 1

HCID 20340335HCID 20340335, compound

Conditions

Temperature
66 °C

Procedure

Into a round bottom flask equipped with magnetic stirrer, reflux condenser and drying tube was charged 20 ml. of dry tetrahydrofuran and 3.2 g. (0.011 moles) of 2-hydroxyethyl 2-cyano-3,3-diphenylacrylate and the solution is rapidly stirred. Then sodium hydride 0.79 g. (0.016 moles) as a 50% oil dispersion was added portionwise. To the resulting suspension was added 5.3 g. (0.044 moles) of allyl bromide and the mixture was heated at reflux (66° C.) for 5.5 hours. Upon cooling, a white insoluble solid (NaBr) was removed by filtration. The organic filtrate was evaporated, leaving as the desired product a pale yellow oil.

Workup

  1. customInto a round bottom flask equipped with magnetic stirrer
  2. temperaturereflux condenser
  3. customdrying tube
  4. additionwas charged 20 ml
  5. additionTo the resulting suspension was added 5.3 g
  6. temperatureUpon cooling
  7. customa white insoluble solid (NaBr) was removed by filtration
  8. customThe organic filtrate was evaporated

Sources & evidence

ORD record
ord-ffadaf8e261c4bb9903b2eedb53264a1
Source dataset
uspto-grants-1980_05
Patent number
US04202834

Reaction notes

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