Water → 7-Methyl-2,3-dihydro-1-benzofuran-3-ol

HRID 431787

Reaktionsgleichung

Reaktionsgleichung von HRID 431787
[Cl-].[CH3:2][S+](C)(C)=O.[H-].[Na+].[OH:9][C:10]1[C:17]([CH3:18])=[CH:16][CH:15]=[CH:14][C:11]=1[CH:12]=[O:13].O>C1COCC1>[CH3:18][C:17]1[C:10]2[O:9][CH2:2][CH:12]([OH:13])[C:11]=2[CH:14]=[CH:15][CH:16]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 24758Sodium hydrideHCID 197819Trimethyloxosulphonium chlorideHCID 5227773-Methylsalicylaldehyde

Produkt 1

HCID 130130607-Methyl-2,3-dihydro-1-benzofuran-3-olAusbeute 45 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a stirred suspension of trimethyl sulfoxonium chloride (3.78 g, 0.03 mole) in dry THF (60 ml) was added sodium hydride (1.16 g, 0.03 mole) and the whole warmed to reflux for 1 h. 2-Hydroxy-3-methyl-benzaldehyde (Lancaster) (4 g, 0.03 mole) was added in 30 ml THF via syringe and the resulting orange suspension stirred at reflux for 5 h. Water (50 ml) was added, and the organics were extracted with ether (3×50 ml). The combined organics were dried (MgSO4), filtered and evaporated in vacuo to an orange oil which was purified by column chromatography using 15-25% EtOAc in pentane to give the title product (2 g, 45%); 1HNMR (400 MHz, CDCl3) δ: 2.2 (s, 3H), 4.45 (m, 2H), 5.3 (m, 1H), 6.8 (t, 1H), 7.1 (d, 1H), 7.2 (d, 1H); LRMS: M+H, 151. (ES+).

Aufarbeitung

  1. temperaturethe whole warmed
  2. temperatureto reflux for 1 h
  3. temperatureat reflux for 5 h
  4. extractionthe organics were extracted with ether (3×50 ml)
  5. dry with materialThe combined organics were dried (MgSO4)
  6. filtrationfiltered
  7. customevaporated in vacuo to an orange oil which
  8. customwas purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-ef22592671fd41bcb5480488d8359655
Quelldatensatz
uspto-grants-2003_12
Patentnummer
US06660756B2

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