反应详情

5-(2-(tert-butyldimethylsilyloxy)ethyl)-2-chlorothiophene-3-carbaldehyde (0.8 g) (example 278, step b) in a mixture of ethanol (50 mL) and triethylamine (0.91 mL) with 10% palladium on carbon catalyst (0.28 g) was stirred vigorously under 4 bar pressure of hydrogen for 18 hours. The mixture was filtered through celite and the filter pad washed with ethanol (50 mL). The combined filtrate and washings were evaporated and azeotroped with toluene (20 mL) to give a yellow oil. The oil was dissolved in DCM (100 mL), manganese dioxide (2.3 g) was added and the resulting suspension refluxed overnight. The mixture was filtered through celite and the filter pad washed with DCM (50 mL). The combined filtrate and washings were evaporated in vacuo to give the subtitled compound as a yellow oil. Yield 0.6 g.

1. filtrationThe mixture was filtered through celite
2. washthe filter pad washed with ethanol (50 mL)
3. customThe combined filtrate and washings were evaporated
4. customazeotroped with toluene (20 mL)
5. customto give a yellow oil
6. temperaturethe resulting suspension refluxed overnight
7. filtrationThe mixture was filtered through celite
8. washthe filter pad washed with DCM (50 mL)
9. customThe combined filtrate and washings were evaporated in vacuo