Tetrahydrofuran → HCID 20470566, compound

To a mixture of sodium hydride (66%, 360 mg, 15 mmol) and tetrahydrofuran (10 mL) was added 2-(4-bromophenyl)ethanol (1.5 g, 7.5 mmol) on an ice bath, the solution was stirred at room temperature for 1 hour. 1-Iodopropane (1.5 mL, 15 mmol) and N,N-dimethylformamide (10 mL) were added to the reaction solution on an ice bath, and the solution was stirred overnight at 45° C. The reaction solution was partitioned with water (100 mL) and heptane (200 mL). The organic layer was separated, and washed with brine. this solvent was evaporated in vacuo, the residue was purified by silica gel column chromatography (heptane:ethyl acetate=30:1), and the title compound (0.80 g, 3.3 mmol, 44%) was obtained as a colorless oil.

1. stirringthe solution was stirred overnight at 45° C
2. customThe reaction solution was partitioned with water (100 mL) and heptane (200 mL)
3. customThe organic layer was separated
4. washwashed with brine
5. customthis solvent was evaporated in vacuo
6. customthe residue was purified by silica gel column chromatography (heptane:ethyl acetate=30:1)

ORD record

ord-189ea01696c1467dbe87a28aab6fea78

Source dataset

uspto-grants-2011_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07932272B2