Triethylamine → 3,3,3-Trifluoro-2-hydroxy-2-[(1-methyl-1,2,3,4-tetrahydro-1-naphthalenyl)methyl]propanal

Temperature

21 °C

To a solution of 3,3,3-trifluoro-2-[(1-methyl-1,2,3,4-tetrahydro-1-naphthalenyl)methyl]-1,2-propanediol (Intermediate 5) (1.6 g, 5.55 mmol) in anhydrous dichloromethane (36 ml), anhydrous dimethylsulphoxide (12 ml) and triethylamine (4.9 ml, 35 mmol) stirred under nitrogen in a bath at 8.5° C., was added pyridine-sulphur trioxide complex (4.45 g, 28 mmol) portionwise over 20 min. The solution was stirred in the ice-water bath for a further 1.5 h and then allowed to warm to 21° C. and stirred for 17 h. The reaction mixture was added to aqueous ammonium chloride solution (100 ml) and dichloromethane (100 ml) and the layers were separated. The aqueous layer was re-extracted with dichloromethane (100 ml) and the combined organic layers were washed successively with water (6×100 ml) and saturated brine (100 ml), dried over anhydrous magnesium sulphate and evaporated. The yellow oil obtained was purified by flash chromatography on a 90 g Biotage cartridge eluting with 5% ether in cyclohexane to give the title compound as an oil (1.24 g, 78%).

1. additionwas added pyridine-sulphur trioxide complex (4.45 g, 28 mmol) portionwise over 20 min
2. customthe layers were separated
3. extractionThe aqueous layer was re-extracted with dichloromethane (100 ml)
4. washthe combined organic layers were washed successively with water (6×100 ml) and saturated brine (100 ml)
5. dry with materialdried over anhydrous magnesium sulphate
6. customevaporated
7. customThe yellow oil obtained
8. customwas purified by flash chromatography on a 90 g Biotage cartridge
9. washeluting with 5% ether in cyclohexane

ORD record

ord-9a7ac5652a494023924c9708f2212f11

Source dataset

uspto-grants-2011_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07902224B2