Water → (R)-alpha-(t-Butyldimethylsilyloxy)-alpha-phenylacetaldehyde

Temperature

-40 °C

20 ml of a 1M hexane solution of diisobutylaluminum hydride were added dropwise at -65° C. and in an atmosphere of nitrogen to a solution of 5.9 g of ethyl (R)-α-(t-butyldimethylsilyloxy)-α-phenylacetate (prepared as described in Preparation 23) in 300 ml of dry hexane, and the resulting mixture was stirred at -40° C. for 4 hours. At the end of this time, 10 ml of a tetrahydrofuran solution containing 1 ml of water was added dropwise to the reaction mixture at -40° C., and then the mixture was stirred at room temperature for 1.5 hours. The reaction mixture was then filtered using a Celite (trade mark) filter aid, and the filtrate was concentrated by evaporation under reduced pressure. The resulting residue was purified by column chromatography through silica gel, using a 1:60 by volume mixture of ethyl acetate and hexane as the eluent, to give the title compound having an Rf=0.64 (thin layer chromatography over silica gel, using a 1:50 by volume mixture of ethyl acetate and hexane).

1. additionwas added dropwise to the reaction mixture at -40° C.
2. stirringthe mixture was stirred at room temperature for 1.5 hours
3. filtrationThe reaction mixture was then filtered
4. filtrationfilter aid
5. concentrationthe filtrate was concentrated by evaporation under reduced pressure
6. customThe resulting residue was purified by column chromatography through silica gel
7. additionby volume mixture of ethyl acetate and hexane as the eluent

ORD record

ord-c895f8921aef4903a381e6ac7ed8d06f

Source dataset

uspto-grants-1997_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05635534