Tetrahydrofuran → 9-ethynylanthracene

HRID 1837394Notes

Reaction equation

HRID 1837394 reaction equation
C[Si](C)(C)[C:3]1[C:4]2[C:9](C=C3[C:16]=1[C:15](C#C)=[CH:14][CH:13]=[CH:12]3)=[CH:8][CH:7]=[CH:6][CH:5]=2.[CH2:21]1[CH2:25]O[CH2:23][CH2:22]1>CO.[OH-].[K+].O>[C:22]([C:21]1[C:25]2[C:16]([CH:3]=[C:4]3[C:9]=1[CH:8]=[CH:7][CH:6]=[CH:5]3)=[CH:15][CH:14]=[CH:13][CH:12]=2)#[CH:23]

Participants

6

Reactant 2

HCID 8028TetrahydrofuranHCID 23497953HCID 23497953, compound

Product 1

HCID 41401999-ethynylanthraceneYield 85.8%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 14797Potassium HydroxideSolvent

Procedure

27 g (0.098 mol) of 9-trimethylsilyl ethynyl anthracene was put into a 1 L round-bottomed flask equipped with a stirrer and dissolved in a mixture of 100 ml of THF and 200 ml of methanol. A solution in which 0.7 g of KOH was dissolved in 7 ml of water was dropped into the resulting solution. The reaction mixture was stirred at room temperature for 12 hours. After the reaction was completed, THF and methanol were removed under a reduced pressure. The reaction mixture was then extracted with methylene chloride. The organic layer was washed with water several times and then dried with anhydrous magnesium sulfate. The solvent was removed to obtain yellow viscous liquid, which was then purified by silica gel column chromatography using hexane as an eluent, to give 17 g (85.8% yield) of the desired product.

Workup

  1. customequipped with a stirrer
  2. additionwas dropped into the resulting solution
  3. customTHF and methanol were removed under a reduced pressure
  4. extractionThe reaction mixture was then extracted with methylene chloride
  5. washThe organic layer was washed with water several times
  6. dry with materialdried with anhydrous magnesium sulfate
  7. customThe solvent was removed
  8. customto obtain yellow viscous liquid, which
  9. customwas then purified by silica gel column chromatography

Sources & evidence

ORD record
ord-6e7dd39bdbfb42588c8a30f3ccb6b797
Source dataset
uspto-grants-2004_08
Patent number
US06780950B2

Reaction notes

Loading…