Isopropanol → 1-(2-Chloro-cyclohex-1-enyl)-ethanol

To a solution of 2-chloro-cyclohex-1-enecarbaldehyde (13.6 mmol) in THF at 0° C. was added methyl magnesium bromide (3M in THF; 5.4 mL, 16.32 mmol). The reaction was stirred under N2 for 1 hour, and then iPrOH (2 mL) was added. The mixture was concentrated, and the residue was diluted with 1N aqueous HCl and extracted with EtOAc. The combined organic layers were washed with saturated aqueous NH4Cl, dried over MgSO4, filtered, and concentrated, and the crude material was purified by silica gel chromatography to give the title compound.

1. concentrationThe mixture was concentrated
2. additionthe residue was diluted with 1N aqueous HCl
3. extractionextracted with EtOAc
4. washThe combined organic layers were washed with saturated aqueous NH4Cl
5. dry with materialdried over MgSO4
6. filtrationfiltered
7. concentrationconcentrated
8. customthe crude material was purified by silica gel chromatography

ORD record

ord-c1de9bb69f974f1984bdc55d78bb03eb

Source dataset

uspto-grants-2012_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08273780B2