Hydrochloric Acid → Methyl 5-Hydroxy-2-tert-butyldimethylsilyloxymethyl-4-methoxyhydrocinnamate

HRID 1898763Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1898763
C([O:4][C:5]1[C:6]([O:26][CH3:27])=[CH:7][C:8]([CH2:17][O:18][Si:19]([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:21])[CH3:20])=[C:9]([CH:16]=1)[CH2:10][CH2:11][C:12]([O:14][CH3:15])=[O:13])(=O)C.C(=O)([O-])[O-].[K+].[K+].Cl>CO.O>[OH:4][C:5]1[C:6]([O:26][CH3:27])=[CH:7][C:8]([CH2:17][O:18][Si:19]([C:22]([CH3:23])([CH3:24])[CH3:25])([CH3:20])[CH3:21])=[C:9]([CH:16]=1)[CH2:10][CH2:11][C:12]([O:14][CH3:15])=[O:13]

Komponenten

6

Edukt 3

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 23372362Methyl 5-acetoxy-2-tert-butyldimethylsilyloxymethyl-4-methoxyhydrocinnamate

Produkt 1

HCID 23372374Methyl 5-Hydroxy-2-tert-butyldimethylsilyloxymethyl-4-methoxyhydrocinnamate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

A mixture of methyl 5-acetoxy-2-tert-butyldimethylsilyloxymethyl-4-methoxyhydrocinnamate (4.64 g) and potassium carbonate (0.16 g) in anhydrous methanol (50 ml) is stirred at 0°-5° C. for about 18 hours, diluted with water, and the pH adjusted to 5 with dilute HCl. The mixture is extracted with ether and the ether solution is washed with brine, dried over magnesium sulfate, filtered and concentrated in vacuo. The residue is purified by HPLC, eluting with 20% ethyl acetate in hexanes to give the desired product.

Aufarbeitung

  1. extractionThe mixture is extracted with ether
  2. washthe ether solution is washed with brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue is purified by HPLC
  7. washeluting with 20% ethyl acetate in hexanes

Quellen und Nachweise

ORD-Eintrag
ord-2114d28bad454af9b4c8e60deb539fb3
Quelldatensatz
uspto-grants-1996_11
Patentnummer
US05571506

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