Water → 2-Ethynyl-1-benzofuran

HRID 2377287Notes

Reaction equation

HRID 2377287 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[C:2]1[C:10]#[C:11][Si](C)(C)C.C(=O)([O-])[O-].[K+].[K+].O>CO>[C:10]([C:2]1[O:1][C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=1)#[CH:11]

Participants

5

Reactant 3

HCID 962WaterHCID 11430Potassium CarbonateHCID 25096393(1-Benzofuran-2-ylethynyl)(trimethyl)silane

Product 1

HCID 138045182-Ethynyl-1-benzofuran

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of Example 652 (0.74 g, 3.47 mmol) and potassium carbonate (1.45 g, 10.41 mmol) in methanol (3 mL) was stirred at room temperature for about 2 hours. The solution was poured into water and was extracted with diethyl ether. The combined organic extracts were dried (MgSO4), filtered and concentrated under vacuum to provide Example 653. 1H NMR (300 MHz, CDCl3) δ 3.49 (s, 1H), 7.01 (s, 1H), 7.25 (m, 1H), 7.35 (m, 1H), 7.46 (m, 1H), 7.56 (m, 1H).

Workup

  1. extractionwas extracted with diethyl ether
  2. dry with materialThe combined organic extracts were dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated under vacuum
  5. customto provide Example 653

Sources & evidence

ORD record
ord-de0e373fffb84929840fc5f117203ec7
Source dataset
uspto-grants-2008_12
Patent number
US07468371B2

Reaction notes

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