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

HRID 1869991Notes

Reaction equation

HRID 1869991 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-cde93479137143899638998aa978441f
Source dataset
uspto-grants-2009_12
Patent number
US07638648B2

Reaction notes

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