Sodium Sulfate → HCID 10942538, compound

Temperature

0 °C

In an atmosphere of argon gas, an ethereal solution (10 ml) of (4S,5S)-4,5-bis(methoxycarbonyl)-1-cyclohexene (1.86 g, 9.4 mmoles) was slowly added at 0° C. to a suspension (100 ml) of lithium aluminum hydride (713 mg, 18.8 mmoles) in ether, and the resulting mixture was stirred at 0° C. for 2 hours. After adding a saturated aqueous solution of sodium sulfate to the reaction mixture and decomposing the excessive reductant, anhydrous sodium sulfate was added and the whole mixture was stirred for a while. After filtering off the inorganic matter and washing the mixture with hot isopropyl alcohol, the filtrate and the washings were united, and the solvent was distilled off therefrom under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:n-hexane=2:1, v/v) and then recrystallized from ethyl acetate-hexane mixture to obtain (4S,5S)4,5-bis(hydroxymethyl)-1-cyclohexene (1.09 g, Yield 82%).

1. additionwas added
2. stirringthe whole mixture was stirred for a while
3. filtrationAfter filtering off the inorganic matter
4. washwashing the mixture with hot isopropyl alcohol
5. distillationthe solvent was distilled off
6. customThe residue was purified by silica gel column chromatography (ethyl acetate
7. customn-hexane=2:1, v/v) and then recrystallized from ethyl acetate-hexane mixture

ORD record

ord-d3eb5126d24e49cd9b34c2d0afd07757

Source dataset

uspto-grants-1994_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05374625