[4-[[tert-butyl(dimethyl)silyl]oxymethyl]cyclohexyl]methanol

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of [4-(tert-butyldimethylsilanyloxymethyl)-cyclohexyl]-methanol (8.5 g) obtained in Step 1 in chloroform (85 mL) was added 1,1,1-tris(acetyloxy)-1,1-dihydro-1,2-benziodoxol-3-(1H)-one (Dess-Martin periodinane; 15.3 g) under ice-cooling, followed by stirring the mixture under ice-cooling for 2.5 hours. After addition of aqueous sodium sulfite solution and aqueous sodium bicarbonate solution, the reaction mixture was filtered through Celite, followed by extraction with ethyl acetate. The organic layer was washed with saturated brine, dried and concentrated. The residue was purified by column chromatography on silica gel (ethyl acetate:hexane (volume ratio)=1:19 to 1:9) to give 4-(tert-butyldimethylsilanyloxymethyl)-cyclohexanecarbaldehyde (6.9 g). cooling cooling for 2.5 hours the reaction mixture was filtered through Celite followed by extraction with ethyl acetate The organic layer was washed with saturated brine dried concentrated The residue was purified by column chromatography on silica gel (ethyl acetate:hexane (volume ratio)=1:19 to 1:9)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of cyclohexane-1,4-dimethanol (10.0 g) in N,N-dimethylformamide (100 mL) were added successively tert-butyldimethylchlorosilane (8.9 g) and imidazole (9.5 g), followed by stirring the reaction mixture at room temperature for 16 hours. To the reaction mixture were added ice and saturated aqueous lithium bromide solution, followed by extraction with diethyl ether. The organic layer was washed with saturated aqueous lithium bromide solution and saturated brine, dried and concentrated. The residue was purified by column chromatography on silica gel (ethyl acetate:hexane (volume ratio)=1:9 to 2:3) to give [4-(tert-butyldimethylsilanyloxymethyl)-cyclohexyl]-methano 1 (8.7 g). followed by extraction with diethyl ether The organic layer was washed with saturated aqueous lithium bromide solution and saturated brine dried concentrated The residue was purified by column chromatography on silica gel (ethyl acetate:hexane (volume ratio)=1:9 to 2:3)