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

HRID 736586

Reaktionsgleichung

Reaktionsgleichung von HRID 736586
[CH:1]([C:3]1[CH:8]=[C:7](Br)[CH:6]=[C:5]([CH:10]=[O:11])[C:4]=1[OH:12])=[O:2].[CH:13]#[C:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24]>C(#N)C.[Cu]I.C1(C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)[Pd][P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH:1]([C:3]1[CH:8]=[C:7]([C:13]#[C:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[CH:6]=[C:5]([CH:10]=[O:11])[C:4]=1[OH:12])=[O:2]

Komponenten

6

Edukt 2

HCID 698211-DodecyneHCID 52602065-Bromo-2-hydroxybenzene-1,3-dicarbaldehyde

Produkt 1

HCID 597108655-(Dodec-1-YN-1-YL)-2-hydroxybenzene-1,3-dicarbaldehydeAusbeute 46 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 178419050HCID 178419050, VerbindungKatalysatorHCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

2,6-Diformyl-4-bromophenol (2.50 g, 10.9 mmol), 1-dodecyne (2.00 g, 12.0 mmol), CuI (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.

Aufarbeitung

  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
  9. dry with materialdried (MgSO4)
  10. concentrationconcentrated under reduced pressure
  11. customThe dark yellow oil was purified by column chromatography on silica gel (25% Et2O in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-81fc3fbce02449e0b0669b26f7226ded
Quelldatensatz
uspto-grants-2009_09
Patentnummer
US07595368B2

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