Potassium Carbonate → 3-tert-Butyl-5-ethynyl-2-isopropoxy-6-methyl-benzaldehyde

HRID 1765858Notes

Reaction equation

HRID 1765858 reaction equation
[C:1]([C:5]1[C:6]([O:20][CH:21]([CH3:23])[CH3:22])=[C:7]([C:10]([CH3:19])=[C:11]([C:13]#[C:14][Si](C)(C)C)[CH:12]=1)[CH:8]=[O:9])([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+]>CO.O1CCCC1>[C:1]([C:5]1[C:6]([O:20][CH:21]([CH3:23])[CH3:22])=[C:7]([C:10]([CH3:19])=[C:11]([C:13]#[CH:14])[CH:12]=1)[CH:8]=[O:9])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 211071563-tert-Butyl-2-isopropoxy-6-methyl-5-trimethylsilanylethynyl-benzaldehyde2×

Product 1

HCID 211071573-tert-Butyl-5-ethynyl-2-isopropoxy-6-methyl-benzaldehydeYield 98.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 3-tert-butyl-2-isopropoxy-6-methyl-5-trimethylsilanylethynyl-benzaldehyde (Intermediate 142, 0.45 g, 1.37 mmol) in methanol (5 mL) and tetrahydrofuran was treated with potassium carbonate (0.2 g, 1.45 mmol) and the resulting reaction mixture was stirred at ambient temperature for 3 h. The reaction mixture was evaporated in vacuo and the residue was extracted with diethyl ether and washed with water and brine. The organic phase was dried, filtered and evaporated in vacuo to afford the title compound (0.35 g, 90%).

Workup

  1. customthe resulting reaction mixture
  2. customThe reaction mixture was evaporated in vacuo
  3. extractionthe residue was extracted with diethyl ether
  4. washwashed with water and brine
  5. customThe organic phase was dried
  6. filtrationfiltered
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-52f3e7c8d6f94371b50c25fd22c194c4
Source dataset
uspto-grants-2007_06
Patent number
US07226951B2

Reaction notes

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