Hexane → 5,6,7-Trimethoxy-2-vinylnaphthalene

HRID 720310Notes

Reaction equation

HRID 720310 reaction equation
[CH3:1]CCCCC.C([Li])(C)(C)C.[CH3:12][O:13][C:14]1[C:23]([O:24][CH3:25])=[C:22]([O:26][CH3:27])[CH:21]=[C:20]2[C:15]=1[CH:16]=[CH:17][C:18]([CH:28]=O)=[CH:19]2>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1COCC1>[CH3:12][O:13][C:14]1[C:23]([O:24][CH3:25])=[C:22]([O:26][CH3:27])[CH:21]=[C:20]2[C:15]=1[CH:16]=[CH:17][C:18]([CH:28]=[CH2:1])=[CH:19]2

Participants

6

Reactant 3

HCID 8058HexaneHCID 218916375,6,7-Trimethoxynaphthalene-2-carbaldehydeHCID 178418306HCID 178418306, compound

Product 1

HCID 218915705,6,7-Trimethoxy-2-vinylnaphthalene

Reagents, catalysts & solvents 2

HCID 74505Methyltriphenyliphosphonium bromideCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

Methyltriphenylphosphonium bromide (2.8 g) was suspended in dry THF (10 mL) under an argon atmosphere, and a 1.7 M hexane solution (3.3 mL) of tert-butyllithium was added to the suspension at −20° C. After stirring the mixture at room temperature for 1 hour, the reaction mixture was cooled again to −20° C., a solution of 5,6,7-trimethoxynaphthalene-2-carboaldehyde (1.26 g) in dry THF (30 mL) was added dropwise thereto, and the mixture was stirred overnight at room temperature. The solvent was distilled off, and water was added to the residue to conduct extraction with ethyl acetate. The resultant organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (ethyl acetate:hexane=1:8) to obtain the title compound.

Workup

  1. temperaturethe reaction mixture was cooled again to −20° C.
  2. stirringthe mixture was stirred overnight at room temperature
  3. distillationThe solvent was distilled off
  4. additionwater was added to the residue
  5. extractionextraction with ethyl acetate
  6. washThe resultant organic layer was washed with water and saturated brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by column chromatography on silica gel (ethyl acetate:hexane=1:8)

Sources & evidence

ORD record
ord-43ecb106b1c4430db3b8ec9a01fd6b29
Source dataset
uspto-grants-2006_11
Patent number
US07135473B2

Reaction notes

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