Trimethyl orthoformate → HCID 67119360, compound

HRID 2076618Notes

Reaction equation

HRID 2076618 reaction equation
[CH:1]([O:6][CH3:7])([O:4][CH3:5])OC.[CH:8]([C:11]1[C:12]([O:19][CH2:20][O:21][CH3:22])=[C:13]([CH:16]=[CH:17][CH:18]=1)C=O)([CH3:10])[CH3:9]>CO.[Cl-].[NH4+]>[CH3:7][O:6][CH:1]([O:4][CH3:5])[C:13]1[CH:16]=[CH:17][CH:18]=[C:11]([CH:8]([CH3:10])[CH3:9])[C:12]=1[O:19][CH2:20][O:21][CH3:22]

Participants

5

Reactant 2

HCID 9005Trimethyl orthoformateHCID 23155341HCID 23155341, compound

Product 1

HCID 67119360HCID 67119360, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 25517Ammonium ChlorideCatalystHCID 887MethanolSolvent

Procedure

Trimethyl orthoformate (2.35 ml, 21.4 mmol) and ammonium chloride (52 mg, 0.98 mmol) were added to a solution of 3-isopropyl-2-(methoxymethoxy)benzaldehyde (4.06 g, 19.5 mmol) which was synthesized according to the method described in literature (James, R. et al., J. Med. Chem., 1980, vol. 23, pp. 1350-1357) in methanol (65 ml), and the mixture was stirred under heating with reflux for 1 hour. The solvent was removed under reduced pressure and a saturated aqueous sodium hydrogencarbonate solution was added to the residue, and the mixture was extracted with ethyl acetate. The organic layer was washed with a saturated aqueous NaCl solution and dried with anhydrous sodium sulfate. The residue obtained by removing the solvent under reduced pressure was purified by silica gel column chromatography (eluting solvent: n-hexane/ethyl acetate=12/0-12/1) to give 1-(dimethoxymethyl)-3-isopropyl-2-(methoxymethoxy)benzene as a colorless oil (4.49 g, yield: 91%).

Workup

  1. customwas synthesized
  2. temperatureunder heating
  3. temperaturewith reflux for 1 hour
  4. customThe solvent was removed under reduced pressure
  5. additiona saturated aqueous sodium hydrogencarbonate solution was added to the residue
  6. extractionthe mixture was extracted with ethyl acetate
  7. washThe organic layer was washed with a saturated aqueous NaCl solution
  8. dry with materialdried with anhydrous sodium sulfate
  9. customThe residue obtained
  10. customby removing the solvent under reduced pressure
  11. customwas purified by silica gel column chromatography (eluting solvent: n-hexane/ethyl acetate=12/0-12/1)

Sources & evidence

ORD record
ord-9d5dd50e3e14401bbe2d2b2f5052f58d
Source dataset
uspto-grants-2011_04
Patent number
US07923573B2

Reaction notes

Loading…