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 5-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-9d8c4de3a5e2416682c6f646072e5a06

Source dataset

uspto-grants-2009_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07476680B2