Triethylamine → rac-3,4-Dihydro-2,5,7,8-tetramethyl-2-{[4-(3-pyridinyl)-phenyl]ethynyl}-2H-1-benzopyran-6-ol

HRID 256841

Reaktionsgleichung

Reaktionsgleichung von HRID 256841
[C:1]([C:3]1([CH3:17])[CH2:8][CH2:7][C:6]2[C:9]([CH3:16])=[C:10]([OH:15])[C:11]([CH3:14])=[C:12]([CH3:13])[C:5]=2[O:4]1)#[CH:2].I[C:19]1[CH:24]=[CH:23][C:22]([C:25]2[CH:26]=[N:27][CH:28]=[CH:29][CH:30]=2)=[CH:21][CH:20]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(N(CC)CC)C>C(#N)C>[CH3:17][C:3]1([C:1]#[C:2][C:19]2[CH:20]=[CH:21][C:22]([C:25]3[CH:26]=[N:27][CH:28]=[CH:29][CH:30]=3)=[CH:23][CH:24]=2)[CH2:8][CH2:7][C:6]2[C:9]([CH3:16])=[C:10]([OH:15])[C:11]([CH3:14])=[C:12]([CH3:13])[C:5]=2[O:4]1

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 126443563-(4-Iodophenyl)pyridineHCID 14478563rac-3,4-dihydro-2-ethynyl-2,5,7,8-tetramethyl-2H-1-benzopyran-6ol

Produkt 1

HCID 15171829rac-3,4-Dihydro-2,5,7,8-tetramethyl-2-{[4-(3-pyridinyl)-phenyl]ethynyl}-2H-1-benzopyran-6-ol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A mixture of 1.15 g of rac-3,4-dihydro-2-ethynyl-2,5,7,8-tetramethyl-2H-1-benzopyran-6-ol, 1.14 g (4 mmol) of 3-(4-iodophenyl)pyridine, 0.2 g of triphenylphosphine, 50 mg of cuprous iodide, 1.5 ml of triethylamine and 20 ml of acetonitrile was degassed with argon for 10 minutes. Palladium acetate, 75 mg, was then added and stirring was continued for 3 hours. The reaction mixture was partitioned between methylene chloride and water. The organic layer was dried and evaporated. The residue was crystallized from ethyl acetate and recrystallized from methanol/ethyl acetate to give colorless crystals with m.p. 190°-192° C.

Aufarbeitung

  1. customwas degassed with argon for 10 minutes
  2. additionPalladium acetate, 75 mg, was then added
  3. customThe reaction mixture was partitioned between methylene chloride and water
  4. customThe organic layer was dried
  5. customevaporated
  6. customThe residue was crystallized from ethyl acetate
  7. customrecrystallized from methanol/ethyl acetate
  8. customto give colorless crystals with m.p. 190°-192° C.

Quellen und Nachweise

ORD-Eintrag
ord-be389ac1631849338c0cc78715d1c37b
Quelldatensatz
uspto-grants-1993_11
Patentnummer
US05260294

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