反应详情

To a suspension of LiAlH4 (219 mg, 5.76 mmol) in THF (35 mL), a solution of 3-(4-hydroxymethyl-2,6-dimethyl-phenyl)-propionic acid (1.0 g, 4.80 mmol, intermediate from Aldehyde 4) in THF (10 mL) is added dropwise. Upon complete addition the suspension is refluxed for 2 h. The suspension is diluted with THF (10 mL) and another portion of LiAlH4 (182 mg, 4.80 mmol) is added. The mixture is refluxed for further two hours, then cooled with an ice-bath. The reaction is carefully quenched by adding sat. aq. NH4Cl solution (2 mL) followed by 2 N aq. HCl until a clear solution forms. The mixture is diluted with water and extracted twice with EA. The combined organic extracts are dried over MgSO4, filtered and the solvent of the filtrate is evaporated to leave 3-(4-hydroxymethyl-2,6-dimethyl-phenyl)-propan-1-ol (920 mg) as a colourless crystalline solid; LC-MS: tR=0.70 min, [M+1−H2O]+=177.20.

1. additionUpon complete addition the suspension
2. temperatureis refluxed for 2 h
3. temperatureThe mixture is refluxed for further two hours
4. temperaturecooled with an ice-bath
5. customThe reaction is carefully quenched
6. additionby adding sat. aq. NH4Cl solution (2 mL)
7. additionThe mixture is diluted with water
8. extractionextracted twice with EA
9. dry with materialThe combined organic extracts are dried over MgSO4
10. filtrationfiltered
11. customthe solvent of the filtrate is evaporated