Propargyl bromide → HCID 89705088, compound

HRID 59674Notes

Reaction equation

HRID 59674 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]([CH2:12][O:13][CH3:14])[C:3]=1[C:4]([O:6][CH3:7])=[O:5].[CH2:15](Br)[C:16]#[CH:17].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH3:14][O:13][CH2:12][C:8]1[CH:9]=[CH:10][CH:11]=[C:2]([O:1][CH2:17][C:16]#[CH:15])[C:3]=1[C:4]([O:6][CH3:7])=[O:5]

Participants

5

Reactant 3

HCID 7842Propargyl bromide2×HCID 11430Potassium CarbonateHCID 89704969Methyl 2-hydroxy-6-methoxymethylbenzoate2×

Product 1

HCID 89705088HCID 89705088, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of methyl 2-hydroxy-6-methoxymethylbenzoate (Intermediate 11, 1.46 g), propargyl bromide (80% solution in toluene, 1.24 mL) and potassium carbonate (1.55 g) in acetone (50 mL) was stirred and heated at reflux for 2 hours. Further propargyl bromide (80% solution in toluene, 0.9 mL) was added and the mixture was stirred and heated at reflux for 2 hours. After cooling, the mixture was filtered and the filtrate was evaporated to dryness. The residue was purified by chromatography on silica, eluting with a mixture of ethyl acetate and pentane with a gradient of 0-30% to give methyl 2-methoxymethyl-6-propargyloxybenzoate (1.34 g) as an oil.

Workup

  1. temperatureheated
  2. temperatureat reflux for 2 hours
  3. stirringthe mixture was stirred
  4. temperatureheated
  5. temperatureat reflux for 2 hours
  6. temperatureAfter cooling
  7. filtrationthe mixture was filtered
  8. customthe filtrate was evaporated to dryness
  9. customThe residue was purified by chromatography on silica
  10. washeluting with a mixture of ethyl acetate and pentane with a gradient of 0-30%

Sources & evidence

ORD record
ord-3f8873ba8bd94228bd3fabc84f4f5e8a
Source dataset
uspto-grants-2016_09
Patent number
US09440943B2

Reaction notes

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