Sodium hydride → HCID 59885608, compound

Temperature

5 °C

Sodium hydride (60 weight %; 1.79 g; 44.8 mmol) is washed with hexanes (3×10 mL) under an argon blanket. DMF (17 mL) is then added at ambient temperature and the stirred slurry is cooled to 5° C. A solution of 4-hydroxyquinoline (5.00 g; 34.4 mmol) in DMF (65 mL) is added dropwise over 10 minutes. The resulting mixture is allowed to warm to ambient temperature over 1 hour affording a clear, reddish-brown solution. A solution of (R)-(−)-glycidyl tosylate (10.22 g; 44.8 mmol) in DMF (50 mL) is added dropwise over 10 minutes. The resulting mixture is stirred at ambient temperature for 20.5 hours, quenched by the addition of saturated aqueous ammonium chloride (25 mL), poured onto water (750 mL), and extracted with ether (3×375 mL). The combined ether layers are washed with saturated aqueous sodium bicarbonate (2×375 mL), then dried over MgSO4, filtered, and concentrated in vacuo. The residue is purified via silica gel chromatography with gradient elution (50%→60% acetone in hexanes) affording the desired product (1.11 g) as a tan solid. ESMS: MH+ 202.2.

1. temperatureto warm to ambient temperature over 1 hour
2. customaffording a clear, reddish-brown solution
3. customquenched by the addition of saturated aqueous ammonium chloride (25 mL)
4. additionpoured onto water (750 mL)
5. extractionextracted with ether (3×375 mL)
6. washThe combined ether layers are washed with saturated aqueous sodium bicarbonate (2×375 mL)
7. dry with materialdried over MgSO4
8. filtrationfiltered
9. concentrationconcentrated in vacuo
10. customThe residue is purified via silica gel chromatography with gradient elution (50%→60% acetone in hexanes)

ORD record

ord-7df4caf27d61441b8b18f4d23d082331

Source dataset

uspto-grants-2004_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06693099B2