Potassium Carbonate → Tert-butyl 2-ethynyl-6-methoxyphenylcarbamate

HRID 1095692Notes

Reaction equation

HRID 1095692 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

HCID 11430Potassium CarbonateHCID 10829462Tert-butyl 2-methoxy-6-((trimethylsilyl)ethynyl)phenylcarbamate

Product 1

HCID 86638604Tert-butyl 2-ethynyl-6-methoxyphenylcarbamateYield 62%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

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%).

Workup

  1. filtrationfiltered
  2. washwashed with DCM (50 mL)
  3. concentrationThe combined organic layers were concentrated
  4. additiondiluted with DCM (20 mL)
  5. filtrationfiltered
  6. washwashed a second time with DCM (50 mL)
  7. concentrationconcentrated
  8. customThe residue was purified by flash chromatography through a pad of silica gel with 10:1 Hexane/EtOAc (500 mL)

Sources & evidence

ORD record
ord-6895bced2787464cb18398dad8c1202a
Source dataset
uspto-grants-2012_03
Patent number
US08138181B2

Reaction notes

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