Triethylamine → 2-[(1-Ethyl-1,2,3,4-tetrahydro-1-naphthalenyl)methyl]-3,3,3-trifluoro-2-hydroxypropanal

To a solution of 2-[(1-ethyl-1,2,3,4-tetrahydro-1-naphthalenyl)methyl]-3,3,3-trifluoro-1,2-propanediol (Intermediate 16) (2.03 g, 6.71 mmol) in anhydrous dichloromethane (50 ml), anhydrous dimethylsulphoxide (50 ml) and triethylamine (5.9 ml, 42 mmol) stirred under nitrogen in an ice-water bath at 9° C., was added pyridine-sulphur trioxide complex (5.37 g, 33 mmol) portionwise over 20 min. The solution was then allowed to warm to room temperature and stirred for 65 h. The reaction mixture was added to aqueous ammonium chloride solution (350 ml) and extracted into dichloromethane (×2). The combined organic layers were washed successively with water (2×200 ml) and saturated brine (2×200 ml), dried over anhydrous magnesium sulphate and evaporated in vacuo. The brown oil obtained was applied to a 50 g silica SPE cartridge eluting with 0 to 100% dichloromethane in heptane gradient to give the title compound as a mixture of diastereomers (380 mg, 19%).

1. additionwas added pyridine-sulphur trioxide complex (5.37 g, 33 mmol) portionwise over 20 min
2. extractionextracted into dichloromethane (×2)
3. washThe combined organic layers were washed successively with water (2×200 ml) and saturated brine (2×200 ml)
4. dry with materialdried over anhydrous magnesium sulphate
5. customevaporated in vacuo
6. customThe brown oil obtained
7. washeluting with 0 to 100% dichloromethane in heptane gradient

ORD record

ord-2c504be608e64a078f4086e23bfecbde

Source dataset

uspto-grants-2011_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07902224B2