Potassium Carbonate → 6-Ethynylnaphthalen-2-ol

HRID 1518405Notes

Reaction equation

HRID 1518405 reaction equation
C[Si]([C:5]#[C:6][C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[CH:13]=[C:12]([OH:17])[CH:11]=[CH:10]2)(C)C.C([O-])([O-])=O.[K+].[K+]>CO.C1COCC1.C(OCC)(=O)C>[C:6]([C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[CH:13]=[C:12]([OH:17])[CH:11]=[CH:10]2)#[CH:5]

Participants

6

Reactant 2

HCID 11430Potassium CarbonateHCID 594475526-((Trimethylsilyl)ethynyl)naphthalen-2-ol

Product 1

HCID 190817686-Ethynylnaphthalen-2-ol

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Compound 110A (770 mg, 3.20 mmol) in MeOH (5 ml) and THF (10 ml) was treated with K2CO3 (885 mg, 6.41 mmol) at room temperature for 3 h. The reaction was diluted with ethyl acetate and washed with water. The organic layer was concentrated and the residue was purified by flash chromatography, eluted with DCM to provide the compound 110B.

Workup

  1. washwashed with water
  2. concentrationThe organic layer was concentrated
  3. customthe residue was purified by flash chromatography
  4. washeluted with DCM

Sources & evidence

ORD record
ord-b26daf207e0a4777895a4cc24c021b56
Source dataset
uspto-grants-2012_07
Patent number
US08232273B2

Reaction notes

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