1-Dodecyne → 5-(Dodec-1-YN-1-YL)-2-hydroxybenzene-1,3-dicarbaldehyde

2,6-Diformyl-4-bromophenol (2.50 g, 10.9 mmol), 1-dodecyne (2.00 g, 12.0 mmol), Cul (65 mg, 0.33 mmol), and bis(triphenylphosphine)palladium)II)dichloride were suspended in degassed acetonitrile (MeCN) (5 mL) and degassed benzene (1 mL). The yellow suspension was sparged with argon for 30 min and degassed Et3N (1 mL) was added. The resulting brown suspension was sealed in a pressure vial, warmed to 80° C. and held there for 12 h. The mixture was then partitioned between EtOAc and KHSO4 solution. The organic layer was separated, washed with brine, dried MgSO4) and concentrated under reduced pressure. The dark yellow oil was purified by column chromatography on silica gel (25% Et2O in hexanes) to give 1.56 g (46%) of the title compound.

1. customdegassed benzene (1 mL)
2. customThe yellow suspension was sparged with argon for 30 min
3. customdegassed Et3N (1 mL)
4. additionwas added
5. customThe resulting brown suspension was sealed in a pressure vial
6. customThe mixture was then partitioned between EtOAc and KHSO4 solution
7. customThe organic layer was separated
8. washwashed with brine, dried MgSO4) and
9. concentrationconcentrated under reduced pressure
10. customThe dark yellow oil was purified by column chromatography on silica gel (25% Et2O in hexanes)

ORD record

ord-2fe543425c5d41608322a71ab1ccb910

Source dataset

uspto-grants-2009_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07563890B2