Potassium Carbonate → 4-Tert-butyl-1-ethynyl-2-nitrobenzene

HRID 1916066Notes

Reaction equation

HRID 1916066 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]#[C:12][Si](C)(C)C)=[C:7]([N+:17]([O-:19])=[O:18])[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+]>CO>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]#[CH:12])=[C:7]([N+:17]([O-:19])=[O:18])[CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 58016188(4-tert-Butyl-2-nitro-phenylethynyl)-trimethyl-silane

Product 1

HCID 580162084-Tert-butyl-1-ethynyl-2-nitrobenzeneYield 81.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(4-tert-Butyl-2-nitro-phenylethynyl)-trimethyl-silane (3.167 g, 11.51 mmol) and potassium carbonate (3.18 g, 23.0 mmol) were stirred in 75 mL methanol for 20 minutes. The resulting mixture was partitioned between ethylacetate and water. The ethylacetate layer was washed with brine, dried over anhydrous MgSO4, concentrated in vacuo, and purified by flash chromatography with gradient elution with 0 to 5% ethylacetate/hexanes to yield 4-tert-Butyl-1-ethynyl-2-nitro-benzene (1.910 g, 9.398 mmol).

Workup

  1. customThe resulting mixture was partitioned between ethylacetate and water
  2. washThe ethylacetate layer was washed with brine
  3. dry with materialdried over anhydrous MgSO4
  4. concentrationconcentrated in vacuo
  5. custompurified by flash chromatography with gradient elution with 0 to 5% ethylacetate/hexanes

Sources & evidence

ORD record
ord-f58ac724bfd34ace8c640834fa15fd13
Source dataset
uspto-grants-2013_12
Patent number
US08618098B2

Reaction notes

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