Sodium ethoxide → 2,3-dihydro-6-fluoro-4-cyano-2-(2-phenylethyl)-4H-1-benzopyran

HRID 2248293Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2248293
[F:1][C:2]1[CH:3]=[CH:4][C:5]2[O:10][CH:9]([CH2:11][CH2:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH2:8][C:7](=O)[C:6]=2[CH:20]=1.C1(C)C(S([CH2:30][N+:31]#[C-])(=O)=O)=CC=CC=1.[O-]CC.[Na+].[Na]>O1CCCC1.C(O)C>[C:30]([CH:7]1[C:6]2[CH:20]=[C:2]([F:1])[CH:3]=[CH:4][C:5]=2[O:10][CH:9]([CH2:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:8]1)#[N:31]

Komponenten

7

Edukt 4

HCID 2723922Sodium ethoxideHCID 5360545SodiumHCID 190944442,3-dihydro-6-fluoro-2-(2-phenylethyl)-4H-1-benzopyran-4-oneHCID 53627694Toluenesulfonylmethyl isocyanide

Produkt 1

HCID 190944432,3-dihydro-6-fluoro-4-cyano-2-(2-phenylethyl)-4H-1-benzopyranAusbeute 29,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittel2×HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

2,3-dihydro-6-fluoro-2-(2-phenylethyl)-4H-1-benzopyran-4-one (8.9 gm) was dissolved in anhydrous tetrahydrofuran, and toluenesulfonylmethylisocyanide (12.9 gm) added, followed by freshly prepared sodium ethoxide in ethanol (prepared from sodium (1.5 gm) in ethanol (60 mL) and the mixture stirred at room temperature overnight. The mixture was then concentrated in vacuo, and the residue partitioned between ethyl acetate and H2O, and the organic layer washed with H2O, brine, dried, filtered and evaporated. The residue was purified by column chromatography (2:1 hexanes/diethyl ether) to yield 4-cyano-2,3-dihydro-6-fluoro-2-(2-phenylethyl)-4H-1-benzopyran (2.7 gm, ir: 2250 cm-1).

Aufarbeitung

  1. concentrationThe mixture was then concentrated in vacuo
  2. customthe residue partitioned between ethyl acetate and H2O
  3. washthe organic layer washed with H2O, brine
  4. customdried
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified by column chromatography (2:1 hexanes/diethyl ether)

Quellen und Nachweise

ORD-Eintrag
ord-dcc432068a9e4d18b8acd0795b0e2e87
Quelldatensatz
uspto-grants-1991_08
Patentnummer
US05039672

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