Sodium Chloride → HCID 12967235, compound

In nitrogen atmosphere, 1.50 ml (11.4 mmol) of diisopropylamin and 6.60 ml (10.6 mmol) of 1.6 M butyllithium hexane were added to 15 ml of THF anhydride at a room temperature, and the mixture was stirred for 30 minutes. Adding 10 ml of THF dissolving 1.48 g (5.32 mmol) of 1-(3-methoxybenzyloxy)-2,2,4,4-tetramethyl-3-pentanon (Compound [49]) at −78° C., the mixture was stirred for 2 hours. The reaction mixture was stirred for 200 minutes with increasing the temperature to a room temperature gradually. The mixture was added to saturated aqueous solution of sodium chloride and extracted with ethyl acetate. The organic layer was washed with saturated aqueous solution of sodium chloride, then dried with magnesium sulfate anhydride and concentrated. The concentrate was applied to a silica gel column and the elution was carried out with the mixture of hexane and ethyl acetate (hexane:ethyl acetate=1:2) to obtain 1.30 g of 3-t-butyl-3-hydroxy-2-(3-methoxyphenyl)-4,4-dimethyl-2,3,4,5-tetrahydrofuran (Compound [50]). Yield 87.8%.

1. stirringthe mixture was stirred for 2 hours
2. stirringThe reaction mixture was stirred for 200 minutes
3. extractionextracted with ethyl acetate
4. washThe organic layer was washed with saturated aqueous solution of sodium chloride
5. dry with materialdried with magnesium sulfate anhydride
6. concentrationconcentrated
7. washthe elution
8. additionwas carried out with the mixture of hexane and ethyl acetate (hexane:ethyl acetate=1:2)

ORD record

ord-62da25b4cb9d498384a9b634376a4e37

Source dataset

uspto-grants-2001_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06218135B1