Triethylamine → 5-(2-(Tert-butyldimethylsilyloxy)ethyl)thiophene-3-carbaldehyde

Participants

Reaction Steps

A slurry of palladium on carbon (10%, 0.28 g) in water (0.5 mL) was added cautiously to a solution of 5-(2-(tert-butyldimethylsilyloxy)ethyl)-2-chlorothiophene-3-carbaldehyde [Aromatic Intermediate 17, step 1)] (0.80 g) and triethylamine (0.91 mL) in ethanol (50 mL) and the resulting mixture stirred overnight under 4 bar pressure of hydrogen. The mixture was filtered through Celite and the filter pad washed with ethanol (10 mL). The combined filtrate and washings were evaporated and azeotroped with toluene (20 mL) to give a yellow oil. The residue was dissolved in DCM (100 mL), manganese dioxide (2.28 g) was added and the resulting suspension heated at reflux overnight. The mixture was filtered through Celite and the filter pad washed with DCM (50 mL). The combined filtrate and washings were evaporated to give the titled compound as a yellow oil. Yield 0.60 g.

Provenance & Evidence