Methyl 2-hydroxy-5-((trimethylsilyl)ethynyl)benzoate → Methyl 5-ethynyl-2-hydroxybenzoate

HRID 742992Notes

Reaction equation

HRID 742992 reaction equation
C[Si]([C:5]#[C:6][C:7]1[CH:8]=[CH:9][C:10]([OH:17])=[C:11]([CH:16]=1)[C:12]([O:14][CH3:15])=[O:13])(C)C.O.O.[F-].[K+]>CN(C=O)C>[C:6]([C:7]1[CH:8]=[CH:9][C:10]([OH:17])=[C:11]([CH:16]=1)[C:12]([O:14][CH3:15])=[O:13])#[CH:5]

Participants

4

Reactant 2

HCID 19423395Methyl 2-hydroxy-5-((trimethylsilyl)ethynyl)benzoateHCID 23708904Potassium fluoride dihydrate

Product 1

HCID 14172485Methyl 5-ethynyl-2-hydroxybenzoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of methyl 5-[(trimethylsilyl)ethynyl]-2-hydroxybenzoate (100 g, 0.57 mol) and potassium fluoride dihydrate (150 g, 1.59 mol) in DMF (600 ml) was stirred for 4 h at room temperature. The solution was extracted with ether (3×400 ml) and the combined ether extracts were washed with 1M HCl (2×200 ml) and water (2×100 ml). The ether layer was dried with Na2SO4 and evaporated to dryness. Yield 66.5 g (93% ).

Workup

  1. extractionThe solution was extracted with ether (3×400 ml)
  2. washthe combined ether extracts were washed with 1M HCl (2×200 ml) and water (2×100 ml)
  3. dry with materialThe ether layer was dried with Na2SO4
  4. customevaporated to dryness

Sources & evidence

ORD record
ord-efe0408eeb354928b54eb67cef324d0a
Source dataset
uspto-grants-1996_09
Patent number
US05556855

Reaction notes

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