Methanol → 3,6-Diethynyl-9-methyl-9H-carbazole

HRID 556135Notes

Reaction equation

HRID 556135 reaction equation
C1COCC1.CO.C[Si]([C:12]#[C:13][C:14]1[CH:15]=[CH:16][C:17]2[N:18]([CH3:33])[C:19]3[C:24]([C:25]=2[CH:26]=1)=[CH:23][C:22]([C:27]#[C:28][Si](C)(C)C)=[CH:21][CH:20]=3)(C)C.[OH-].[Na+]>C(Cl)Cl.O>[C:27]([C:22]1[CH:21]=[CH:20][C:19]2[N:18]([CH3:33])[C:17]3[C:25]([C:24]=2[CH:23]=1)=[CH:26][C:14]([C:13]#[CH:12])=[CH:15][CH:16]=3)#[CH:28]

Participants

7

Reactant 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 59806152HCID 59806152, compound

Product 1

HCID 598061623,6-Diethynyl-9-methyl-9H-carbazoleYield 81.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A mixed solution containing dist. THF and dist. MeOH (dist. THF/dist. MeOH=3/1: 4 mL) as well as dist. H2O (0.1 mL) were added to and dissolved into 3,6-bis(trimethylsilylethynyl)-9-methylcarbazole (173 mg, 0.46 mmol) obtained in Synthesis example 12. Then, NaOH (35 mg, 0.88 mmol) was added, and the resultant mixed solution was stirred under a nitrogen atmosphere at room temperature for 4 hours to obtain a reaction mixture. After that, the reaction mixture was diluted with CH2Cl2. Then, an organic layer was washed with dist. H2O and sat. NaCl, and was dried with MgSO4. The dried organic layer was filtered and concentrated to obtain a crude product. Subsequently, the obtained crude product was separated and purified by silica gel column chromatography (hexane/EtOAc=5/1) to obtain 3,6-diethynyl-9-methylcarbazole (86 mg, 81% yield).

Workup

  1. additionA mixed solution containing dist
  2. customobtained in Synthesis example 12
  3. additionthe resultant mixed solution
  4. customto obtain a reaction mixture
  5. washThen, an organic layer was washed with dist
  6. dry with materialH2O and sat. NaCl, and was dried with MgSO4
  7. filtrationThe dried organic layer was filtered
  8. concentrationconcentrated
  9. customto obtain a crude product
  10. customSubsequently, the obtained crude product
  11. customwas separated
  12. custompurified by silica gel column chromatography (hexane/EtOAc=5/1)

Sources & evidence

ORD record
ord-04b639c9ef2642aebbdeabe36155f592
Source dataset
uspto-grants-2011_11
Patent number
US08053588B2

Reaction notes

Loading…