3,4,5-TRIMETHYL-4-HEPTANOL synthesis

Yield:60836-08-0 51%

Reaction Conditions:

with magnesium;copper(II) oxide in tetrahydrofuran at 65; for 4 h;chemoselective reaction;Barbier Coupling Reaction;

Steps:

Synthesis of tertiary alcohol compounds

General procedure: To a three-necked, 50 mL flaskequipped with a magnetic stirring bar, 15 mL of THF, 2.5 mmol of ester (1 equiv), 0.375 mmol of CuO (15% equiv), 7.5 mmol of aryl halides and magnesium chips (3 equiv) or 15 mmol of alkyl bromides and magnesium chips (6 equiv) were added. The reaction mixture was heated at 65 °C for 4 h. The progress of the reaction was monitored by TLC. Then, the reaction was quenched by saturated aqueous NH₄Cl (5 mL), extracted with AcOEt (10 mL × 3), dried over sodium sulfate, filtered, and evaporated to give the raw product. Pure product could be obtained by TLC with petroleum /AcOEt = 5/1 as eluent.

References:

Gao, Fei;Deng, Xiang-Jun;Tang, Yu;Tang, Jin-Peng;Yang, Jun;Zhang, Yuan-Ming [Tetrahedron Letters,2014,vol. 55,# 4,p. 880 - 883] Location in patent:supporting information