Methyl iodide → 1-(Isoquinolin-5-yl)ethanol

To a mixture of Mg turnings (0.2 g, 7.9 mmol) in ether (10 mL) was added MeI (1.13 g, 7.9 mmol) slowly at RT under an inert atmosphere. After being stirred for 1 h at RT, the reaction mixture was cooled to −10° C. and a solution of isoquinoline-5-carbaldehyde (0.5 g, 3.18 mmol) in ether (10 mL) was added. The reaction mixture was then stirred for an additional hour at RT, quenched with saturated NH4Cl solution and extracted with EtOAc (3×50 mL). The combined organic layers were washed with water and brine, dried over Na2SO4, filtered and concentrated in vacuo to obtain the crude product. The crude material was purified via silica gel column chromatography using 30% ethyl acetate in hexanes to afford 1-(isoquinolin-5-yl)ethanol (0.53 g, 97%) as an off-white solid.

1. temperaturethe reaction mixture was cooled to −10° C.
2. stirringThe reaction mixture was then stirred for an additional hour at RT
3. customquenched with saturated NH4Cl solution
4. extractionextracted with EtOAc (3×50 mL)
5. washThe combined organic layers were washed with water and brine
6. dry with materialdried over Na2SO4
7. filtrationfiltered
8. concentrationconcentrated in vacuo
9. customto obtain the crude product
10. customThe crude material was purified via silica gel column chromatography

ORD record

ord-7ac68687a3e74ebbb9e91eb9a2001f71

Source dataset

uspto-grants-2013_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08481532B2