Tributylphosphine → Ethyl [(4-{[1-(3-bromo-2-methylphenyl)pentyl]oxy}-2-methylphenyl)oxy]acetate

To a solution of 1-(3-bromo-2-methylphenyl)-1-pentanol (495 mg, 1.92 mmol) in anhydrous THF (40 mL) under nitrogen at 0° C. was added portion-wise ethyl (4-hydroxy-2-methylphenoxy)acetate (405 mg, 1.93 mmol), followed by slow addition (over 25 min) of ADDP (971 mg, 3.85 mmol) and drop-wise addition of tributylphosphine (0.96 mL, 3.85 mmol). The resulting mixture was then stirred for 16 h with gradual warming to ambient temperature. The solvent was then removed under vacuum and the residue partitioned between EtOAc (100 mL) and water (150 mL), the layers separated, and the aqueous re-extracted with EtOAc (100 mL). The combined organic layer was then dried (Na2SO4), filtered and reduced under vacuum and the resulting residue purified by SPE (silica, 50 g cartridge), eluting with cyclohexane:EtOAc (gradient 99:1 to 4:1) to afford the title compound as a colourless oil (495 mg).

1. customThe solvent was then removed under vacuum
2. customthe residue partitioned between EtOAc (100 mL) and water (150 mL)
3. customthe layers separated
4. extractionthe aqueous re-extracted with EtOAc (100 mL)
5. dry with materialThe combined organic layer was then dried (Na2SO4)
6. filtrationfiltered
7. customthe resulting residue purified by SPE (silica, 50 g cartridge)
8. washeluting with cyclohexane

ORD record

ord-dc0ae2c7e8ea4414bcf2d2c08f902c3a

Source dataset

uspto-grants-2008_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07338960B2