Potassium Carbonate → Methyl 4-ethynylbenzoate

HRID 1180815Notes

Reaction equation

HRID 1180815 reaction equation
C[Si]([C:5]#[C:6][C:7]1[CH:16]=[CH:15][C:10]([C:11]([O:13][CH3:14])=[O:12])=[CH:9][CH:8]=1)(C)C.C(=O)([O-])[O-].[K+].[K+]>CO>[C:6]([C:7]1[CH:16]=[CH:15][C:10]([C:11]([O:13][CH3:14])=[O:12])=[CH:9][CH:8]=1)#[CH:5]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 640161Methyl 4-trimethylsilylethynylbenzoate

Product 1

HCID 640163Methyl 4-ethynylbenzoateYield 98.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution at 0° C. under nitrogen of XXXI (9.05 g, 38.95 mmol) in MeOH (280 ml) was added potassium carbonate (1.62 g, 11.72 mmol). After 3 h, the reaction mixture was concentrated and directly purified by flash chromatography on silica gel (CH2Cl2:100) to afford the title compound XXXII (6.16 g, 38.46 mmol, 98% yield) as a pale yellow solid. 1H NMR: (400 MHz, CDCl3) δ (ppm): AB system (δA=7.98, δB=7.54, JAB=8.6 Hz, 4H), 3.93 (s, 3H), 3.24 (s, 1H).

Workup

  1. concentrationthe reaction mixture was concentrated
  2. customdirectly purified by flash chromatography on silica gel (CH2Cl2:100)

Sources & evidence

ORD record
ord-c87e14f3d32c42b4bea3a6c0acb27a6c
Source dataset
uspto-grants-2007_10
Patent number
US07282608B2

Reaction notes

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