Acetic Anhydride → 5-Methyl-4-(1-acetoxytridecyl)-2-trimethylsilylfuran

HRID 488234

Reaktionsgleichung

Reaktionsgleichung von HRID 488234
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13].[Mg].[CH3:15][C:16]1[O:20][C:19]([Si:21]([CH3:24])([CH3:23])[CH3:22])=[CH:18][C:17]=1[CH:25]=[O:26].[C:27](OC(=O)C)(=[O:29])[CH3:28]>O1CCCC1>[CH3:15][C:16]1[O:20][C:19]([Si:21]([CH3:22])([CH3:24])[CH3:23])=[CH:18][C:17]=1[CH:25]([O:26][C:27](=[O:29])[CH3:28])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13]

Komponenten

6

Edukt 4

HCID 7918Acetic AnhydrideHCID 89191-BromododecaneHCID 5462224MagnesiumHCID 157445905Methyl-2-trimethylsilyl-4-furaldehyde

Produkt 1

HCID 194331855-Methyl-4-(1-acetoxytridecyl)-2-trimethylsilylfuran

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

A mixture of 1-bromododecane (261 mg, 0.11 mmol) and magnesium turnings (27 mg, 0.11 mmol) in tetrahydrofuran (7 ml) was refluxed under argon for 1 hour. After cooling to room temperature, a solution of 5-methyl-2-trimethylsilyl-4-furaldehyde (158.6 mg, 0.87 mmol) in tetrahydrofuran (1 ml) was added, followed by acetic anhydride (0.25 ml, 2.6 mmol) after 1 hour. Stirring was continued at room temperature overnight and the mixture was quenched with water. Extraction (ethyl ether) and evaporation of the dried (magnesium sulphate) extracts gave an oil, which was purified by preparative TLC (20×20 cm, 1000 micron silica plate; developed with 5% ethyl ether/hexane). The title ester was obtained as a light yellow oil.

Aufarbeitung

  1. temperaturewas refluxed under argon for 1 hour
  2. customthe mixture was quenched with water
  3. extractionExtraction (ethyl ether) and evaporation of the
  4. dry with materialdried (magnesium sulphate)
  5. customextracts gave an oil, which
  6. customwas purified by preparative TLC (20×20 cm, 1000 micron silica plate; developed with 5% ethyl ether/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-dca08df96bca4e8999c4587933fcfd3a
Quelldatensatz
uspto-grants-1994_03
Patentnummer
US05298633

Verknüpfte Notizen

Wird geladen…