Methanol → 1-(3-Tert-butyldiphenylsilyloxymethyl-2,4-dichlorophenyl)-2-formylpyrrole

To a solution of 1-(3-tert-butyldiphenylsilyloxymethyl-2,4-dichlorophenyl)-2-cyanopyrrole (2.44 g) in dichloromethane (25 ml) was added diisobutylaluminum hydride (1.5 M solution in toluene, 4.9 ml) under nitrogen atmosphere in water bath, and the mixture was stirred for 30 minutes at the same temperature. The reaction mixture was cooled in ice water bath, and to the mixture were added dropwise methanol (1 ml) and water (1 ml). The mixture was stirred for 1 hour, quenched with 1N sodium hydroxide solution and extracted with chloroform. The organic layer was washed with a saturated aqueous sodium hydrogen carbonate solution and brine, dried over magnesium sulfate and evaporated in vacuo. The residue was chromatographed on silica gel eluting with a mixture of n-hexane and ethyl acetate (20:1, V/V) to give 1-(3-tert-butyldiphenylsilyloxymethyl-2,4-dichlorophenyl)-2-formylpyrrole (1.9 g) as an oil.

1. stirringThe mixture was stirred for 1 hour
2. customquenched with 1N sodium hydroxide solution
3. extractionextracted with chloroform
4. washThe organic layer was washed with a saturated aqueous sodium hydrogen carbonate solution and brine
5. dry with materialdried over magnesium sulfate
6. customevaporated in vacuo
7. customThe residue was chromatographed on silica gel eluting with a mixture of n-hexane and ethyl acetate (20:1, V/V)

ORD record

ord-9a56cfeb1583429fb110453d0ef26f0e

Source dataset

uspto-grants-2000_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06100284