Dimethylformamide → HCID 15635484, compound

Temperature

-10 °C

To a stirred mixture of DMF (100 mL) and THF (100 mL), was added solid potassium tert-butoxide (17.96 g, 0.16 mol). After all of the solid had dissolved, the solution was cooled to ≦5° C. and 3-hydroxypyridine (14.25 g, 0.15 mol) was added all at once. After stirring for 10 minutes, the mixture was cooled to −10° C. and SEM-Cl, 25 g, 0.15 mol) was added dropwise at such a rate that the internal temperature remained at ≦−5° C. After the addition was complete, the mixture was stirred at 0° C. for 1 hour, then at room temperature for 2 hours. The mixture was poured into water (600 mL), then extracted with ether (3×150 mL). The ether extracts were combined, washed sequentially with 2N NaOH (100 mL), water (50 mL), and saturated NaCl solution (100 mL), dried (MgSO4) and concentrated to give a brown liquid. Distillation gave the desired ether 9 as a colorless liquid (20.8 g), b.p. 95-99° C. @ 0.03 mm Hg.

1. dissolutionAfter all of the solid had dissolved
2. temperaturethe solution was cooled to ≦5° C.
3. customremained at ≦−5° C
4. additionAfter the addition
5. stirringthe mixture was stirred at 0° C. for 1 hour
6. waitat room temperature for 2 hours
7. extractionextracted with ether (3×150 mL)
8. washwashed sequentially with 2N NaOH (100 mL), water (50 mL), and saturated NaCl solution (100 mL)
9. dry with materialdried (MgSO4)
10. concentrationconcentrated
11. customto give a brown liquid
12. distillationDistillation

ORD record

ord-7b3fab8f021f433893a70836fadac1ee

Source dataset

uspto-grants-2006_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07034035B2