Tetrahydrofuran → (8-Methyl-1,4,7,9-tetraoxaspiro[4.5]dec-8-yl)methanol

HRID 31587Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 31587
C1COCC1.C([O:14][CH2:15][C:16]1([CH3:26])[O:25][CH2:24][C:19]2([O:23][CH2:22][CH2:21][O:20]2)[CH2:18][O:17]1)(=O)C1C=CC=CC=1.[OH-].[Na+]>CO>[CH3:26][C:16]1([CH2:15][OH:14])[O:17][CH2:18][C:19]2([O:20][CH2:21][CH2:22][O:23]2)[CH2:24][O:25]1

Komponenten

5

Edukt 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 59792389(8-Methyl-1,4,7,9-tetraoxaspiro[4.5]dec-8-yl)methyl benzoate

Produkt 1

HCID 59792532(8-Methyl-1,4,7,9-tetraoxaspiro[4.5]dec-8-yl)methanolAusbeute 90,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To a THF (10 ml) and methanol (5 ml) solution of the (8-methyl-1,4,7,9-tetraoxaspiro[4.5]dec-8-yl)methyl benzoate (1.92 g, 6.52 mmol) obtained in the step (5b), a 1N aqueous sodium hydroxide solution (10 ml, 10 mmol) was added and stirred at room temperature for one hour. The reaction mixture was extracted with dichloromethane (50 ml) four times, dried over anhydrous sodium sulfate, and then, concentrated. The obtained crude product was purified by silica gel column chromatography (elution solvent: heptane/ethyl acetate=1/1-0/1 gradient) and desired fractions were concentrated to obtain the title compound (1.12 g, 90.0% yield) as a white solid.

Aufarbeitung

  1. extractionThe reaction mixture was extracted with dichloromethane (50 ml) four times
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationconcentrated
  4. customThe obtained crude product
  5. customwas purified by silica gel column chromatography (elution solvent: heptane/ethyl acetate=1/1-0/1 gradient)
  6. concentrationdesired fractions were concentrated

Quellen und Nachweise

ORD-Eintrag
ord-1838b8e973424ec6be874e2b75b82e37
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07425634B2

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