Propargyl bromide → Methyl-3-propargyloxy-2-naphthoate

HRID 1618

Reaction equation

HRID 1618 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:14]([OH:15])=[CH:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=1)=[O:4].[H-].[Na+].[CH2:18](Br)[C:19]#[CH:20]>C1COCC1>[CH3:1][O:2][C:3]([C:5]1[C:14]([O:15][CH2:20][C:19]#[CH:18])=[CH:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=1)=[O:4]

Participants

5

Reactant 3

HCID 7842Propargyl bromideHCID 24758Sodium hydrideHCID 70163Methyl 3-hydroxy-2-naphthoate

Product 1

HCID 54262446Methyl-3-propargyloxy-2-naphthoateYield 35%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methyl-3-hydroxy-2-naphthoate (2.63 g, 0.013 mol) was dissolved in dry THF (80 ml) and treated with sodium hydride (80%) ((0.398 g, 0.013 mol), with stirring under N2. After 0.5 h, propargyl bromide (80% in toluene) (2.57 ml 0.017 mol) was added and the mixture heated to reflux. After 20 h, the reaction mixture was allowed to cool and then evaporated under reduced pressure. The residue was then evaporated under reduced pressure. The residue was then partitioned between EtOAc and water. The aqueous layer was then extracted with EtOAc (1×), and the combined organic layers were dried (Na2SO4) and evaporated to given an orange oil. Crystallisation of the oil from petrol (60/80) diethyl ether provided the title compound as a pale yellow solid (1.0 gg, 35%).

Workup

  1. temperaturethe mixture heated to reflux
  2. waitAfter 20 h
  3. temperatureto cool
  4. customevaporated under reduced pressure
  5. customThe residue was then evaporated under reduced pressure
  6. customThe residue was then partitioned between EtOAc and water
  7. extractionThe aqueous layer was then extracted with EtOAc (1×)
  8. dry with materialthe combined organic layers were dried (Na2SO4)
  9. customevaporated
  10. customCrystallisation of the oil from petrol (60/80) diethyl ether

Sources & evidence

ORD record
ord-33fdd502bd9b4b6ab4abded4f14a5ab2
Source dataset
uspto-grants-1998_03
Patent number
US05726187

Linked notes

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