[(4-Methoxy-3-methylphenyl)ethynyl](trimethyl)silane → 4-Ethynyl-1-methoxy-2-methylbenzene

HRID 271123Notes

Reaction equation

HRID 271123 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]#[C:10][Si](C)(C)C)=[CH:5][C:4]=1[CH3:15]>CCCC[N+](CCCC)(CCCC)CCCC.[F-]>[C:9]([C:6]1[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[C:4]([CH3:15])[CH:5]=1)#[CH:10]

Participants

3

Reactant 1

HCID 44817931[(4-Methoxy-3-methylphenyl)ethynyl](trimethyl)silane

Product 1

HCID 448179324-Ethynyl-1-methoxy-2-methylbenzeneYield 99.4%

Reagents, catalysts & solvents 1

HCID 2724141Tetrabutylammonium FluorideSolvent

Procedure

A solution of [(4-methoxy-3-methylphenyl)ethynyl](trimethyl)silane (7.167 g) tetrahydrofuran was treated with TBAF (30 mL, 1.0 M solution in tetrahydrofuran), stirred for 1 hour and evaporated to dryness. The residue was dissolved in diethyl ether, washed with water, dried over anhydrous magnesium sulfate and evaporated. This residue was applied on a pad of silica and eluted with hexane:ethyl acetate (4:1). The elute was evaporated to dryness to give the alkyne intermediate as a brown solid (4.77 g). The compound was characterized by LCMS analysis. LCMS Conditions: HP 1100 HPLC system; Waters Xterra MS C18, 2 mm (i.d.)×50 mm (length), 3.5 um column, set at 50° C.; Flow rate 1.0 mL/min; Solvent A: 0.02% NH4OH in water; Solvent B 0.02% NH4OH in ACN; Gradient: Time O: 10% B; 2.5 min 90% B; 3 min 90% B; Sample concentration: ˜2.0 mM; Injection volume: 5 uL; Detection: 220 nm, 254 nm DAD

Workup

  1. customevaporated to dryness
  2. dissolutionThe residue was dissolved in diethyl ether
  3. washwashed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customevaporated
  6. washeluted with hexane:ethyl acetate (4:1)
  7. customThe elute was evaporated to dryness

Sources & evidence

ORD record
ord-f6d4b1f87fe84cd7bd436be8988c3f37
Source dataset
uspto-grants-2008_11
Patent number
US07452885B2

Reaction notes

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