Triethylamine → HCID 18510240, compound

HRID 1371046Notes

Reaction equation

HRID 1371046 reaction equation
[O:1]=[C:2]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH2:3][C:4]1[CH:13]=[CH:12][C:7]([C:8]([O:10]C)=[O:9])=[CH:6][CH:5]=1.[CH3:20][O:21]C(OC)OC.[CH3:27]C1(C)C2(CS(O)(=O)=O)C(CC1CC2)=O.CCN(CC)CC>CO>[CH3:27][O:1][C:2]([O:21][CH3:20])([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH2:3][C:4]1[CH:13]=[CH:12][C:7]([C:8]([OH:10])=[O:9])=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 9005Trimethyl orthoformateHCID 18462Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)-HCID 13397273HCID 13397273, compound

Product 1

HCID 18510240HCID 18510240, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of methyl 4(2-oxo-2-phenylethyl)benzoate (1 g, 3.9 mmole) in MeOH (40 mL) was added trimethylorthoformate 10 mL and CSA (50 mg). The reaction mixture was refluxed for 6 h. The mixture was cooled, then Et3N (0.5 mL) was added, and the mixture concentrated. The residue was dissolved in THF and stirred overnight. The reaction was quenched with ACOH (1 mL) and 40 mL pH 7 phosphate buffer. The organic phase was dried (Na2SO4), filtered, and evaporated to yield the title compound 1.1 g.

Workup

  1. temperatureThe reaction mixture was refluxed for 6 h
  2. temperatureThe mixture was cooled
  3. concentrationthe mixture concentrated
  4. dissolutionThe residue was dissolved in THF
  5. customThe reaction was quenched with ACOH (1 mL) and 40 mL pH 7 phosphate buffer
  6. dry with materialThe organic phase was dried (Na2SO4)
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-d520ae0d3de04613a28aa2506186c2af
Source dataset
uspto-grants-2003_06
Patent number
US06583126B2

Reaction notes

Loading…