Methyl morpholine oxide → 2-(Tert-butyl-dimethyl-silanyloxymethyl)-propenal

2-(Tert-butyl-dimethyl-silanyloxymethyl)-prop-2-en-1-ol (6 g, 29.7 mmol) prepared in example 99a was dissolved in dichloromethane (296 mL) containing both the molecular sieves (4 A) (Aldrich) and N-methyl morpholine oxide (5.2 g, 44.47 mmol). After stirring the mixture for 1 h, (Tetra-n-butyl ammonium perruthenate) (0.47 g, 1.48 mmol) (Aldrich) was added and the reaction mixture was stirred at room temperature for 1 h. Then another batch of (Tetra-n-butyl ammonium per-ruthenate) (0.23 g, 0.74 mmol) was added and the mixture was stirred at room temperature for another 1 h. The reaction mixture was diluted with dichloromethane. The organic layer was washed with Na2S2O3 solution, brine and saturated copper (II) sulfate solution, then dried over dried over MgSO4, filtered and concentrated. The residue was purified with chromatography to give 2-(tert-butyl-dimethyl-silanyloxymethyl)-propenal to as colorless oil (Yield 1.3 g, 22%).

1. stirringthe reaction mixture was stirred at room temperature for 1 h
2. stirringthe mixture was stirred at room temperature for another 1 h
3. washThe organic layer was washed with Na2S2O3 solution, brine and saturated copper (II) sulfate solution
4. customdried
5. dry with materialover dried over MgSO4
6. filtrationfiltered
7. concentrationconcentrated
8. customThe residue was purified with chromatography

ORD record

ord-ecfaf161a3b54a698904999a366ed1eb

Source dataset

uspto-grants-2009_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07495007B2