Methanol → HCID 58612420, compound

HRID 2223765Notes

Reaction equation

HRID 2223765 reaction equation
CO.[CH:3]([O:8][CH3:9])([O:6][CH3:7])OC.[C:10]([C:14]1[CH:15]=[C:16](C(=O)C)[CH:17]=[C:18]([Cl:22])[C:19]=1[O:20][CH3:21])([CH3:13])([CH3:12])[CH3:11].[C:26](=O)([O-])[O-].[K+].[K+]>C12(CS(O)(=O)=O)C(C)(C)C(CC1)CC2=O.CCCCCCC.O>[C:10]([C:14]1[C:19]([O:20][CH3:21])=[C:18]([Cl:22])[CH:17]=[C:16]([C:3]([O:6][CH3:7])([O:8][CH3:9])[CH3:26])[CH:15]=1)([CH3:13])([CH3:11])[CH3:12]

Participants

8

Reactant 4

HCID 887MethanolHCID 9005Trimethyl orthoformateHCID 11430Potassium CarbonateHCID 58612418HCID 58612418, compound

Product 1

HCID 58612420HCID 58612420, compoundYield 485.3%

Reagents, catalysts & solvents 3

HCID 18462Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)-CatalystHCID 962WaterSolventHCID 8900HeptaneSolvent

Procedure

Methanol (1.4 mL), and trimethyl orthoformate (1.79 g, 16.95 mmol) were added to 1-(3-tert-butyl-5-chloro-4-methoxyphenyl)ethanone (1.36 g, 5.65 mmol), followed by stirring at room temperature. In addition, (±)-10-camphorsulfonic acid [(±)-CSA] (65 mg, 0.282 mmol, 5 mol %) was added, followed by 2 hours of stirring. Potassium carbonate (156 mg, 1.128 mmol) was added. After 40 minutes of stirring, water (10 mL) and n-heptane (10 mL) were added, and the solution was separated. After washing the organic layer with water (10 mL), the solvent was evaporated (50° C.) to obtain 1.57 g of the subject compound as a yellow oily substance (yield: 96.9%).

Workup

  1. stirringof stirring
  2. stirringAfter 40 minutes of stirring
  3. customthe solution was separated
  4. washAfter washing the organic layer with water (10 mL)
  5. customthe solvent was evaporated (50° C.)

Sources & evidence

ORD record
ord-9135e33491574fbeabf2c44b9e913f04
Source dataset
uspto-grants-2008_05
Patent number
US07375236B2

Reaction notes

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