Trimethyl orthoformate → Methyl 3,3-dimethoxycyclobutane-1-carboxylate

HRID 546172Notes

Reaction equation

HRID 546172 reaction equation
O=C1[CH2:5][CH:4]([C:6]([OH:8])=[O:7])[CH2:3]1.[CH:9]([O:14][CH3:15])([O:12][CH3:13])OC.O.[C:17]1(C)C=CC(S(O)(=O)=O)=CC=1>CO>[CH3:17][O:8][C:6]([CH:4]1[CH2:3][C:9]([O:12][CH3:13])([O:14][CH3:15])[CH2:5]1)=[O:7]

Participants

5

Reactant 3

HCID 9005Trimethyl orthoformateHCID 521998p-Toluenesulfonic acid monohydrateHCID 49133583-Oxocyclobutane-1-carboxylic acid

Product 1

HCID 10487446Methyl 3,3-dimethoxycyclobutane-1-carboxylateYield 97%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To the solution of 3-oxo-cyclobutanecarboxylic acid (1.0 g, 8.77 mmol) in methanol (12 ml) was added trimethyl orthoformate (6 ml, 58.29 mmol) and a catalytic amount of p-toluenesulfonic acid monohydrate. The reaction was stirred at reflux for 2 h. After such a time it was cooled and concentrated in vacuo to remove the methanol. The remaining residue was dissolved in ether and then washed with a saturated aqueous sodium bicarbonate solution, dried over sodium sulfate, filtered and concentrated in vacuo to afford 3,3-dimethoxy-cyclobutanecarboxylic acid methyl ester (1.48 g, 97%) as a yellow oil: 1H NMR (300 MHz, CDCl3) δ ppm 2.33-2.51 (m, 4H, 2×CH2), 2.82-2.97 (m, 1H, CH), 3.16 (s, 3H, OCH3), 3.18 (s, 3H, OCH3), 3.71 (s, 3H, CO2CH3).

Workup

  1. temperatureat reflux for 2 h
  2. temperatureAfter such a time it was cooled
  3. concentrationconcentrated in vacuo
  4. customto remove the methanol
  5. dissolutionThe remaining residue was dissolved in ether
  6. washwashed with a saturated aqueous sodium bicarbonate solution
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-584d5dfb395e40dd81f8cd396caecc47
Source dataset
uspto-grants-2011_05
Patent number
US07935699B2

Reaction notes

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