Hydrochloric Acid → Methylenechloride Hexane

Temperature

-78 °C

A THF (120 mL) solution of (R,R)-2,2′-bismethoxymethoxy-1,1′-binaphthol (Compound 2) (46 mmol) was charged to a 200 mL flask and cooled to −78° C., N,N,N′,N′-tetramethylethylenediamine (66 mmol) was added, after which n-butyllithium was added dropwise. The mixture was stirred for 30 minutes at 0° C., a THF solution of N,N-dimethylformamide was added dropwise at −78° C., and the mixture was stirred for 30 minutes. The temperature was increased to 0° C. and the mixture was stirred for 40 minutes. Saturated ammonium chloride aqueous solution and 1 N hydrochloric acid were added. The mixture was extracted with diethyl ether. The organic layer was dried with anhydrous sodium sulfate, the solvent was distilled off, and the residue was purified by silica gel chromatography. The product was then recrystallized from methylene chloride/hexane (yield 67 percent).

1. stirringthe mixture was stirred for 30 minutes
2. temperatureThe temperature was increased to 0° C.
3. stirringthe mixture was stirred for 40 minutes
4. extractionThe mixture was extracted with diethyl ether
5. dry with materialThe organic layer was dried with anhydrous sodium sulfate
6. distillationthe solvent was distilled off
7. customthe residue was purified by silica gel chromatography

ORD record

ord-20d0b329332b48ef9270f5394a9ca55e

Source dataset

uspto-grants-2011_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07964743B2