1-methoxy-2-methyl-1-trimethylsilyloxypropane → HCID 69135147, compound

HRID 2054445Notes

Reaction equation

HRID 2054445 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][N:6]=[C:5]([CH:9]=[O:10])[CH:4]=1.[CH3:11][O:12][CH:13]([O:17][Si](C)(C)C)[CH:14]([CH3:16])[CH3:15]>ClCCl.FC(F)(F)S([O-])(=O)=O.[Sc+3].FC(F)(F)S([O-])(=O)=O.FC(F)(F)S([O-])(=O)=O>[CH3:11][O:12][C:13](=[O:17])[C:14]([CH3:16])([CH3:15])[CH:9]([OH:10])[C:5]1[CH:4]=[C:3]([O:2][CH3:1])[CH:8]=[CH:7][N:6]=1

Participants

5

Reactant 2

HCID 112290981-methoxy-2-methyl-1-trimethylsilyloxypropaneHCID 123253904-Methoxypyridine-2-carboxaldehyde

Product 1

HCID 69135147HCID 69135147, compound

Reagents, catalysts & solvents 2

HCID 2734571Scandium(III) triflateCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of 0.58 g of 4-methoxypyridine-2-carbaldehyde (Ashimori et al., Chem. Pharm. Bull. 38, 2446-2458 (1990)) and 21 mg of scandium trifluoromethanesulfonate in 14 ml of dichloromethane is treated dropwise with 0.9 ml of 1-methoxy-2-methyl-1-trimethylsilyloxypropane under ice-cooling. After 10 min the cooling bath is removed and the mixture is stirred for 18 h. Thereafter, 12 ml of methanol and 12 ml of aqueous hydrochloric acid (3 M) are added and stirring is continued for further 14 h. The solvents are removed in vacuo, the residue is dissolved in dichloromethane and washed with saturated aqueous sodium hydrogencarbonate solution. The organic layer is dried using sodium sulfate and concentrated to give 0.845 g of the title compound as a colorless oil. MS: 240.0 (MH+). TLC: Rf=0.46 (toluene/acetone 2:1).

Workup

  1. temperaturecooling
  2. customAfter 10 min the cooling bath is removed
  3. additionThereafter, 12 ml of methanol and 12 ml of aqueous hydrochloric acid (3 M) are added
  4. stirringstirring
  5. waitis continued for further 14 h
  6. customThe solvents are removed in vacuo
  7. dissolutionthe residue is dissolved in dichloromethane
  8. washwashed with saturated aqueous sodium hydrogencarbonate solution
  9. customThe organic layer is dried
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-baa51dd8fa324f98a418efb10a70caa7
Source dataset
uspto-grants-2008_02
Patent number
US07329677B2

Reaction notes

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