Methanol → 1-(Benzyloxy)-4-(prop-2-yn-1-yl)benzene

HRID 1927243Notes

Reaction equation

HRID 1927243 reaction equation
CO.[CH2:3]([O:10][C:11]1[CH:16]=[CH:15][C:14]([CH2:17][C:18]#[C:19][Si](C)(C)C)=[CH:13][CH:12]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.C(=O)([O-])[O-].[K+].[K+]>O>[CH2:3]([O:10][C:11]1[CH:12]=[CH:13][C:14]([CH2:17][C:18]#[CH:19])=[CH:15][CH:16]=1)[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 11430Potassium CarbonateHCID 42642731(3-(4-Benzyloxy-phenyl)-prop-1-ynyl)-trimethylsilane

Product 1

HCID 592553841-(Benzyloxy)-4-(prop-2-yn-1-yl)benzeneYield 90.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of methanol (20 mL) of (3-(4-benzyloxy-phenyl)-prop-1-ynyl)-trimethyl-silane (910 mg) described in Manufacturing Example 12-1 was added potassium carbonate (850 mg) at room temperature, which was stirred for 4 hours and 10 minutes at room temperature. Water was added to the reaction solution, which was then extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate, and then the solvent was evaporated under a reduced pressure. The residue was purified by silica gel column chromatography (heptane:ethyl acetate=20:1) to obtain the titled compound (620 mg).

Workup

  1. extractionwas then extracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under a reduced pressure
  5. customThe residue was purified by silica gel column chromatography (heptane:ethyl acetate=20:1)

Sources & evidence

ORD record
ord-a0a6cc44b82648abb94aced07439f929
Source dataset
uspto-grants-2012_05
Patent number
US08183264B2

Reaction notes

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