Water → 4,5-difluoro-2-methyl-7-pentyl-7H-furo[3,2-f]chromene

HRID 2244852Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2244852
[F:1][C:2]1[C:3]([F:15])=[C:4]2[O:8][C:7]([CH3:9])=[CH:6][C:5]2=[C:10]([CH:13]=O)[C:11]=1[OH:12].[CH:16](B(O)O)=[CH:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22].C(NCC1C=CC=CC=1)C1C=CC=CC=1.O>O1CCOCC1>[F:15][C:3]1[C:2]([F:1])=[C:11]2[C:10]([CH:13]=[CH:16][CH:17]([CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[O:12]2)=[C:5]2[CH:6]=[C:7]([CH3:9])[O:8][C:4]=12

Komponenten

6

Edukt 4

HCID 962WaterHCID 7656DibenzylamineHCID 27734421-Hepteneboronic acidHCID 592152776,7-Difluoro-5-hydroxy-2-methylbenzofuran-4-carbaldehyde

Produkt 1

HCID 592152654,5-difluoro-2-methyl-7-pentyl-7H-furo[3,2-f]chromene

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

4.0 g (18.6 mmol) of 6,7-difluoro-5-hydroxy-2-methylbenzofuran-4-carbaldehyde are stirred for 20 h at 90° C. together with 3.21 g (22.6 mmol) of 1-hepteneboronic acid and 0.72 ml (3.73 mmol) of dibenzylamine in 95 ml of 1,4-dioxane. Water is added to the reaction mixture, which is then extracted with MTBE. The organic phase is separated off, and the aqueous phase is extracted with MTBE. The combined organic phases are washed with water and sat. sodium chloride soln. The solution is dried using sodium sulfate and concentrated to dryness. The crude product is firstly purified by column chromatography (SiO2, 1-chlorobutane) and subsequently crystallised from methanol, giving 4,5-difluoro-2-methyl-7-pentyl-7H-furo[3,2-f]chromene as a yellow, crystalline solid.

Aufarbeitung

  1. extractionis then extracted with MTBE
  2. customThe organic phase is separated off
  3. extractionthe aqueous phase is extracted with MTBE
  4. washThe combined organic phases are washed with water and sat. sodium chloride soln
  5. customThe solution is dried
  6. concentrationconcentrated to dryness
  7. customThe crude product is firstly purified by column chromatography (SiO2, 1-chlorobutane)
  8. customsubsequently crystallised from methanol

Quellen und Nachweise

ORD-Eintrag
ord-37fc2ebd75394edc9fd60d941317f662
Quelldatensatz
uspto-grants-2010_03
Patentnummer
US07678929B2

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