Water → 2-(3,4-Dimethoxyphenyl)ethyl 2,2,2-trichloroethanimidate

A 500 mL 2-necked round bottom flask equipped with an argon inlet, rubber septum and magnetic stir bar was charged with NaH (80% dispersion, 5.2 g, 173.3 mmol). NaH was washed with anhydrous hexanes (15 mL) prior to the addition of 50 mL of anhydrous CH2Cl2 and of 3,4-dimethoxyphenethyl alcohol (20.0 g, 109.8 mmol) in anhydrous CH2Cl2 (30 mL). The solution was allowed to stir at r.t. for 75 min. The solution was then cooled to 0° C. prior to the dropwise addition of trichloroacetonitrile (16.5 mL, 23.8 g, 164.7 mmol) at 0° C. The solution was stirred for 15 min at 0° C. and 2 hr at room temperature. Distilled water (150 mL) was slowly added dropwise to quench the reaction. The aqueous layer was then extracted with CH2Cl2 (4×100 mL). The combined organic extracts were washed with brine (100 mL), dried over anhydrous MgSO4 and concentrated by rotary evaporation to afford a brown syrup (26.8 g, 95%). The product was allowed to solidify overnight at −20° C. Rf 0.74 (EtOAc-hexanes, 1:2, v/v).

1. customA 500 mL 2-necked round bottom flask equipped with an argon inlet
2. washNaH was washed with anhydrous hexanes (15 mL)
3. additionto the addition of 50 mL of anhydrous CH2Cl2
4. temperatureThe solution was then cooled to 0° C.
5. stirringThe solution was stirred for 15 min at 0° C. and 2 hr at room temperature
6. customto quench
7. customthe reaction
8. extractionThe aqueous layer was then extracted with CH2Cl2 (4×100 mL)
9. washThe combined organic extracts were washed with brine (100 mL)
10. dry with materialdried over anhydrous MgSO4
11. concentrationconcentrated by rotary evaporation

ORD record

ord-a03cb1a910d9497a9e778ff5e0321b65

Source dataset

uspto-grants-2011_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08058304B2