Water → HCID 86702775, compound

Temperature

65 °C

p-Methylphenethyltriphenylphosphonium bromide (2.90 g, 6.29 mmol, 1.0 equiv.) in THF (12 mL), was cooled to 0° C. After adding n-BuLi (1.6 M in hexanes, 3.9 mL, 6.29 mmol, 1.0 equiv.) at 0° C., the red solution was stirred at 65° C. for 1 h. The mixture was re-cooled to 0° C., 2-methylundecanal (1.74 g, 9.43 mmol, 1.5 equiv.) in THF (5 mL) was added, and the mixture was stirred at 65° C. for 16 h. After addition of H2O, the aqueous layer was extracted with cyclohexane (2×), the combined organic phases were washed with brine, dried (MgSO4), filtered and the filtrate was concentrated. The residue was purified by flash chromatography on SiO2 (cyclohexane/EtOAc 997:3) to yield 1.24 g (69%) of the title compound as a colorless oil.

1. temperatureThe mixture was re-cooled to 0° C.
2. stirringthe mixture was stirred at 65° C. for 16 h
3. extractionthe aqueous layer was extracted with cyclohexane (2×)
4. washthe combined organic phases were washed with brine
5. dry with materialdried (MgSO4)
6. filtrationfiltered
7. concentrationthe filtrate was concentrated
8. customThe residue was purified by flash chromatography on SiO2 (cyclohexane/EtOAc 997:3)

ORD record

ord-7a8fd12443c4426792820d4950106c9c

Source dataset

uspto-grants-2015_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09193935B2