Acetone → HCID 59636235, compound

Temperature

-10 °C

Butyl Lithium (10.28 mL, 16.455 mmol) was added to a solution of DIPA (2.66 mL, 18.98 mmol) in THF (25 mL) at −78° C. The reaction mixture was stirred at −10° C. for 10 minutes, followed by the addition of 3-bromo-pyridine (500 mg, 2.212 mmol) in THF (10 mL) at −100° C. The reaction mixture was stirred for a further 15 minutes at −90° C. and was followed by the addition of acetone (1.675 mL, 22.78 mmol) in THF (10 mL) at −78° C. with stirring over a period of 1 hour. The reaction was monitored by TLC (5% ethylacetate in hexane). The reaction mixture was quenched with aqueous NaHCO3 solution and extracted with ethylacetate. The organic layer was dried over Na2SO4 and concentrated. Purification by column chromatography on silica gel (15% ethylacetate in hexane) afforded 200 mg of 2-(3-bromo-pyridin-4-yl)-propan-2-ol (11% yield).

1. stirringThe reaction mixture was stirred for a further 15 minutes at −90° C.
2. stirringwith stirring over a period of 1 hour
3. customThe reaction mixture was quenched with aqueous NaHCO3 solution
4. extractionextracted with ethylacetate
5. dry with materialThe organic layer was dried over Na2SO4
6. concentrationconcentrated
7. customPurification by column chromatography on silica gel (15% ethylacetate in hexane)

ORD record

ord-bc42fb178bdf4ffa974954c7920d10b5

Source dataset

uspto-grants-2014_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

USRE045173E1