Sodium Hydroxide → HCID 23365411, compound

HRID 1080736Notes

Reaction equation

HRID 1080736 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[C:14]#[C:15][Si](C)(C)C)=[CH:4][CH:3]=1.[OH-].[Na+]>CO>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[C:14]#[CH:15])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 23365462HCID 23365462, compound

Product 1

HCID 23365411HCID 23365411, compoundYield 66.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 5.23 g (19.8 mmol) of 4-methyl-2'-trimethylsilylethynyl-1,1'-biphenyl in 60 mL of methanol was treated with 6 mL of 1.25N aqueous sodium hydroxide. The reaction mixture was stirred at room temperature for 30 minutes and evaporated under vacuum. The residue was extracted with ether. The combined ether extracts were washed with water, dried over magnesium sulfate and evaporated under vacuum. The residue was purified by chromatography over silica gel, eluting will hexane, to yield 2.52 g (13.1 mmol, 66%) of the product. FAB-MS: calculated from C15H12 192; found 191 (M-1). 1H NMR (200 MHz, CDCl3): 2.40 (s, 3H), 5.26 (s, 1H), 7.3 (m, 8H).

Workup

  1. customevaporated under vacuum
  2. extractionThe residue was extracted with ether
  3. washThe combined ether extracts were washed with water
  4. dry with materialdried over magnesium sulfate
  5. customevaporated under vacuum
  6. customThe residue was purified by chromatography over silica gel
  7. washeluting will hexane

Sources & evidence

ORD record
ord-884a5e2bb16c4d42ac52bc84e0bd6768
Source dataset
uspto-grants-1996_12
Patent number
US05583130

Reaction notes

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