Toluene → 1,2-Decanediol

Temperature

0 °C

To a well-stirred solution of bis-1,4-(9'-O-dihydroquinidine)phthalazine (7.8 mg, 0.01 mmol), potassium ferricyanide (0.99 g, 3 mmol), potassium carbonate (0.42 g, 3 mmol), and osmium tetroxide (0.1 mL of a 0.1M toluene solution, 0.01 mmol) in 15 mL of a tert-butyl alcohol-water (1:1, v/v) at 0° C., 1-decene (0.14 g, 0.19 mL, 1 mmol) was added in one portion. The mixture was stirred for 24 h at 0° C. Solid sodium sulfite (1.5 g) was added and the mixture was stirred for an additional hour, and then warmed up to room temperature. Ethyl acetate (10 mL) was added to the reaction mixture, and aqueous layer was extracted with ethyl acetate (3×5 mL). Combined organic layer was dried over anhydrous magnesium sulfate, and concentrated in vacuo. Crude product was purified by flash chromatography (silica gel, hexanes/EtOAc) to afford decane 1,2-diol as a white solid (0.145 g, 83%). HPLC analysis of the bis-Mosher ester of this crude decane 1,2 diol gave 84% ee.

1. stirringthe mixture was stirred for an additional hour
2. temperaturewarmed up to room temperature
3. extractionwas extracted with ethyl acetate (3×5 mL)
4. dry with materialCombined organic layer was dried over anhydrous magnesium sulfate
5. concentrationconcentrated in vacuo
6. customCrude product was purified by flash chromatography (silica gel, hexanes/EtOAc)

ORD record

ord-5d317fd0c8aa4f019316bfb9a8cfe508

Source dataset

uspto-grants-1993_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05260461