Potassium Carbonate → Tert-butyl 2-ethynyl-6-methoxyphenylcarbamate
Reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([C:9]#[C:10][Si](C)(C)C)[C:4]=1[NH:15][C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19].C([O-])([O-])=O.[K+].[K+]>CO>[C:9]([C:5]1[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[C:4]=1[NH:15][C:16](=[O:22])[O:17][C:18]([CH3:20])([CH3:19])[CH3:21])#[CH:10]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To tert-butyl 2-methoxy-6-((trimethylsilyl)ethynyl)phenylcarbamate (4.21 g, 13.2 mmol) in MeOH (30 mL) was added K2CO3 (9.11 g, 65.9 mmol). The reaction was stirred for 30 minutes, then filtered and washed with DCM (50 mL). The combined organic layers were concentrated and diluted with DCM (20 mL), filtered, washed a second time with DCM (50 mL), then concentrated. The residue was purified by flash chromatography through a pad of silica gel with 10:1 Hexane/EtOAc (500 mL), affording the desired product (62%).