Water → (1,2,3,4-Tetrahydroquinolin-7-yl)methanol

Participants

Reaction Conditions

Reaction Steps

To a cooled (0° C.) solution 1 g (5.23 mmol) of methyl 1,2,3,4-tetrahydroquinoline-7-carboxylate in THF (10 ml) was added 20.92 ml, (20.92 mmol) of a solution of DIBAL-H in THF. The reaction mixture was stirred for 2 hr at 0° C. Additional DIBAL-H in THF (15.69 ml, 15.69 mmol) was added. The reaction mixture was allowed to warm to 20° C. and stirring was continued for 16 hr. The reaction mixture was treated with 30 mL of 10% aqueous sodium potassium tartrate and stirred for 1 h. Water was added and the mixture was extracted with AcOEt. The organic layer was dried over MgSO4 and concentrated under reduced pressure to give (1,2,3,4-tetrahydroquinolin-7-yl)methanol. HPLC (Method H) Rt=2.74 min; MS (Method A) [M+H]+=164.1

Provenance & Evidence