Toluene → 2-Methyl-2-(2-thienyl)propan-1-ol

A solution of 2-methyl-2-thiophen-2-yl-propionic acid methyl ester (2.085 g, 11.32 mmol) in CH2Cl2 (55 mL) at 0° C. is treated with diisobutylaluminum hydrde (Dibal-H, 1.0 M PhMe, 24.0 mL, 24.0 mmol) and warmed to rt after 4 min. After 1.5 h the reaction mixture is cooled to 0° C. and quenched with 1N tartaric acid (50 mL) and stirred for 2 d. The layers are separated and the aqueous layer is extracted with CH2Cl2 (1×50 mL). The combined extracts are dried over MgSO4, filtered, and concentrated. The residue is loaded onto silica gel and eluted with hexanes using a gradient of 0% to 75% EtOAc to give 2-methyl-2-thiophen-2-yl-propan-1-ol (1.494 g, 84%) as a clear oil.

1. temperatureAfter 1.5 h the reaction mixture is cooled to 0° C.
2. customquenched with 1N tartaric acid (50 mL)
3. customThe layers are separated
4. extractionthe aqueous layer is extracted with CH2Cl2 (1×50 mL)
5. dry with materialThe combined extracts are dried over MgSO4
6. filtrationfiltered
7. concentrationconcentrated
8. washeluted with hexanes using a gradient of 0% to 75% EtOAc

ORD record

ord-01b0fa2f2009458db759df18a024f421

Source dataset

uspto-grants-2011_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08084489B2