Ammonia → HCID 18674821, compound

HRID 1789155Notes

Reaction equation

HRID 1789155 reaction equation
[C-:1]#[C-:2].[Li+].[Li+].N.Br[CH2:7][CH2:8][CH:9]([O:12][CH3:13])[O:10][CH3:11]>>[CH3:11][O:10][CH:9]([O:12][CH3:13])[CH2:8][CH2:7][C:1]#[CH:2]

Participants

4

Reactant 3

HCID 222Ammonia2×HCID 1189323-Bromopropionaldehyde dimethylacetalHCID 178462446HCID 178462446, compound

Product 1

HCID 18674821HCID 18674821, compound

Procedure

To an equivalent quantity of lithium acetylide in liquid NH3 55 g (0.3 mol) of 1-bromo-3,3-dimethoxypropane were added in 30 minutes. Subsequently, stirring was continued for a further 2 hours, after which the NH3 was allowed to evaporate and the residue was dissolved in a mixture of ice and water. The mixture was extracted with ether and the combined organic layers were dried and concentrated by evaporation. The residue was distilled under reduced pressure and 11.5 g of 1,1-dimethoxy-4-pentyne were obtained.

Workup

  1. customto evaporate
  2. dissolutionthe residue was dissolved in a mixture of ice and water
  3. extractionThe mixture was extracted with ether
  4. customthe combined organic layers were dried
  5. concentrationconcentrated by evaporation
  6. distillationThe residue was distilled under reduced pressure

Sources & evidence

ORD record
ord-9aceded8345a480cbb20b84ecb25dc5a
Source dataset
uspto-grants-1987_08
Patent number
US04687599

Reaction notes

Loading…