4-(Hydroxymethyl)cyclohexan-1-one → HCID 23263401, compound

To a stirred solution of 4-(hydroxymethyl)cyclohexanone (1.0 g, 7.8 mmol) in THF (20 mL) was added methyl magnesium bromide (3.0 M in Et2O, 7.8 mL, 23.4 mmol) dropwise at 0° C. for 5 min. The mixture was allowed to warm to room temperature and stirred at the same temperature for 2 h. The reaction mixture was quenched with saturated aqueous NH4Cl and extracted with EtOAc (2×20 mL). The combined organic layers were washed with water (20 mL), brine (20 mL), dried over anhydrous Na2SO4 and concentrated under reduced pressure. The residue was purified by column chromatography (silica gel, 80% EtOAc/hexane as eluent) to provide compound A112-1 (300 mg, 27%) as a white solid.

1. customThe reaction mixture was quenched with saturated aqueous NH4Cl
2. extractionextracted with EtOAc (2×20 mL)
3. washThe combined organic layers were washed with water (20 mL), brine (20 mL)
4. dry with materialdried over anhydrous Na2SO4
5. concentrationconcentrated under reduced pressure
6. customThe residue was purified by column chromatography (silica gel, 80% EtOAc/hexane as eluent)
7. customto provide compound A112-1 (300 mg, 27%) as a white solid

ORD record

ord-88018603200c492b9d1410baa2aadad4

Source dataset

uspto-grants-2016_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09365522B2