Reaction #162539

Reaction equation

2-chloro-7-fluoroquinoline-3-carbaldehyde

MeMgBr

→

1-(2-chloro-7-fluoroquinolin-3-yl)-ethanol

Solvents

THF

Conditions

Workup

1. 1
   Otherthe reaction was quenched with NH4Cl solution
2. 2
   Extractionextracted with Et2O (300 mL and 100 mL)
3. 3
   WashThe organic layers were washed with water, brine
4. 4
   Dryingdried over Na2SO4
5. 5
   Concentrationconcentrated
6. 6
   Otherrecrystallized from EtOAc (100 mL) and hexane (1 L)

Procedure

A suspension of 2-chloro-7-fluoroquinoline-3-carbaldehyde (44.7 g, 213 mmol) in THF (600 mL) was treated with MeMgBr (78.0 mL, 234 mmol 1.1 eq) at −20° C. After stirring overnight, the reaction was quenched with NH4Cl solution and extracted with Et2O (300 mL and 100 mL). The organic layers were washed with water, brine, dried over Na2SO4, concentrated and recrystallized from EtOAc (100 mL) and hexane (1 L). A pale yellow solid of 1-(2-chloro-7-fluoroquinolin-3-yl)-ethanol was obtained (41 g, 85%). Mass Spectrum (ESI) m/e=226 (M+1).

Source