Tetrabutylammonium Fluoride → 2-(2-Hydroxyethyl)-5-[2-(phenylmethoxy)ethyl]furan

HRID 2110426Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2110426
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.CC([Si](C)(C)[O:24][CH2:25][CH2:26][C:27]1[O:28][C:29]([CH2:32][CH2:33][O:34][CH2:35][C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)=[CH:30][CH:31]=1)(C)C>C1COCC1>[OH:24][CH2:25][CH2:26][C:27]1[O:28][C:29]([CH2:32][CH2:33][O:34][CH2:35][C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)=[CH:30][CH:31]=1

Komponenten

4

Edukt 2

HCID 2724141Tetrabutylammonium FluorideHCID 587458712-[2-[[(1,1-Dimethylethyl)dimethylsilyl]oxy]ethyl]-5-[2-(phenylmethoxy)ethyl]furan

Produkt 1

HCID 218751402-(2-Hydroxyethyl)-5-[2-(phenylmethoxy)ethyl]furanAusbeute 99,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Tetrabutylammonium fluoride (1.0M in THF, 3.06 mL, 3.06 mmol) was added to the solution of compound 255D (1.1 g, 3.06 mmol) in 10 mL of THF at 0° C. The reaction mixture was stirred at rt for 10 minutes, quenched by sat. NH4Cl and extracted with ether (3×). The combined extracts were dried over Na2SO4. Purification by flash chromatography on silica gel eluting with 10% EtOAc/90% CH2Cl2 gave 750 mg (3.05 mmol, 99.6%) of compound 255E as a light yellow oil.

Aufarbeitung

  1. customquenched by sat. NH4Cl
  2. extractionextracted with ether (3×)
  3. dry with materialThe combined extracts were dried over Na2SO4
  4. customPurification by flash chromatography on silica gel eluting with 10% EtOAc/90% CH2Cl2

Quellen und Nachweise

ORD-Eintrag
ord-9e51a104e3354a4ead6349c1709e8e4c
Quelldatensatz
uspto-grants-2009_04
Patentnummer
US07517904B2

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