Water → 1-(2-Methoxy-4-nitrophenyl)propan-2-ol

Participants

Reaction Conditions

Reaction Steps

To a stirred −78° C. solution of TiCl4 (1.0 M in CH2Cl2, 1.43 mL, 1.43 mmol) in anhydrous Et2O (7 mL) was added MeLi (1.6 M in Et2O, 0.9 mL, 1.43 mmol) dropwise over a period of 20 min. The reaction mixture was allowed to slowly warm to −30° C. at which point a solution of 2-(2-methoxy-4-nitrophenyl)acetaldehyde (275 mg, 1.43 mmol) (prepared as described in PCT WO 2000/73288 A1) in anhydrous Et2O (0.750 mL) was added dropwise and allowed slowly warm to −10° C. The reaction mixture was poured into cold water and extracted with Et2O (3×50 mL). The combined ether extracts were washed with water (1×100 mL), dried over anhydrous MgSO4 and concentrated under reduced pressure to afford 0.253 g (85%) of the title compound as an orange solid. 1H NMR (500 MHz, CDCl3) δ 1.25 (d, J=6.0 Hz, 3 H), 1.62 (br. s., 1 H), 2.81 (dd, J=13.2, 7.7 Hz, 1 H), 2.89-2.94 (m, 1 H), 3.93 (s, 3 H), 4.06-4.15 (m, 1 H), 7.32 (d, J=8.2 Hz, 1 H), 7.72 (d, J=2.2 Hz, 1 H), 7.82 (dd, J=8.2, 2.2 Hz, 1 H); HPLC (Method #1): 2.68 min retention time, (89%); LCMS (ES): m/z 194 [M−H2O+H]+.

Provenance & Evidence