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

HRID 1645526Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1645526
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-f5fed74336364628846698e36a78636a
Quelldatensatz
uspto-grants-2012_02
Patentnummer
US08124780B2

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