Water → HCID 57515857, compound

Temperature

-78 °C

2,2,6,6-Tetramethylpiperidine (8.26 ml, 49.0 mmol) was dissolved with 270 ml THF and 1-butyllithium (14.1 ml, 35.4 mmol) was added at −78° C. The mixture was stirred for 10 min in an ice bath and cooled back to −78° C. A solution of 2-(2-fluoro-2-methylpropyl)-5-(methoxymethoxy)pyridine (5.8000 g, 27.2 mmol) in 20 ml THF was added dropwise and the reaction was stirred for 20 min. Acetylaldehyde (7.65 ml, 136 mmol) was added to the dark red solution and the color disappeared. Stirring was continued for 20 min and the mixture was hydrolyzed with 50 ml of water. The mixture was warmed to RT and extracted 3× with CH2Cl2 (300 ml each). The combined organic extracts were dried over MgSO4 and evaporated and purified via glass col. chrom. (30-80% EtOAc in hex.) to provide 1-(2-(2-fluoro-2-methylpropyl)-5-(methoxymethoxy)pyridin-4-yl)ethanol a white solid. MS m/z: 258.2 (M+1).

1. additionwas added at −78° C
2. stirringthe reaction was stirred for 20 min
3. stirringStirring
4. waitwas continued for 20 min
5. temperatureThe mixture was warmed to RT
6. extractionextracted 3× with CH2Cl2 (300 ml each)
7. dry with materialThe combined organic extracts were dried over MgSO4
8. customevaporated
9. custompurified via glass col

ORD record

ord-a8bbf4a9261e4b56838631feb90bb8b3

Source dataset

uspto-grants-2012_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08173810B2