2-Bromo-6-methoxynaphthalene → HCID 19877637, compound

HRID 1886254Notes

Reaction equation

HRID 1886254 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8](Br)[CH:7]=[CH:6]2.[H-].[Ca+2].[H-].[C:17]([O:24][CH3:25])(=[O:23])[CH2:18][CH2:19][CH2:20][C:21]#[CH:22]>C(NCC)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8]([C:22]#[C:21][CH2:20][CH2:19][CH2:18][C:17]([O:24][CH3:25])=[O:23])[CH:7]=[CH:6]2

Participants

5

Reactant 3

HCID 787862-Bromo-6-methoxynaphthaleneHCID 534077Methyl 5-hexynoateHCID 3033859Calcium hydride

Product 1

HCID 19877637HCID 19877637, compound

Reagents, catalysts & solvents 1

HCID 8021DiethylamineSolvent

Procedure

Into a solution of 2.51 g (9.2 mmol) of 6-methoxy-2-naphthyl bromide in 31 ml of diethylamine distilled with calcium hydride were charged 324 mg (0.46 mmol) of bistriphenylphosphine palladium dichloride and 192 mg of cupric iodide (1.01 mmol), followed by stirring. To the mixture was gradually added 1.06 g (9.4 mmol) of methyl 5-hexynoate, and the mixture was stirred at room temperature overnight (about 15 hours). Diethylamine was evaporated under a reduced pressure, to the residue were added ethyl acetate and water, and the mixture was extracted with ethyl acetate. Anhydrous magnesium sulfate was introduced into the organic layer for drying.

Workup

  1. stirringthe mixture was stirred at room temperature overnight (about 15 hours)
  2. customDiethylamine was evaporated under a reduced pressure, to the residue
  3. additionwere added ethyl acetate and water
  4. extractionthe mixture was extracted with ethyl acetate
  5. additionAnhydrous magnesium sulfate was introduced into the organic layer
  6. customfor drying

Sources & evidence

ORD record
ord-c33bdde671b14d7eb592b6168e06a5f6
Source dataset
uspto-grants-1992_09
Patent number
US05149859

Reaction notes

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