Sodium Bicarbonate → HCID 89704969, Verbindung

HRID 59675

Reaktionsgleichung

Reaktionsgleichung von HRID 59675
Br[CH2:2][C:3]1[CH:12]=[CH:11][CH:10]=[C:9]([O:13][Si](C(C)(C)C)(C)C)[C:4]=1[C:5]([O:7][CH3:8])=[O:6].[C:21](=O)(O)[O-:22].[Na+]>CO>[OH:13][C:9]1[CH:10]=[CH:11][CH:12]=[C:3]([CH2:2][O:22][CH3:21])[C:4]=1[C:5]([O:7][CH3:8])=[O:6]

Komponenten

4

Edukt 2

HCID 516892Sodium BicarbonateHCID 25170261Methyl 2-bromomethyl-6-(tert-butyldimethylsilyloxy)benzoate2×

Produkt 1

HCID 89704969HCID 89704969, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

A solution of methyl 2-bromomethyl-6-(tert-butyldimethylsilyloxy)benzoate (Intermediate 12, 4.26 g) in methanol (63 mL) was stirred and heated at reflux overnight. After cooling, the mixture was basified by addition of solid sodium bicarbonate and then evaporated to dryness. The residue was triturated with DCM and filtered. The filtrate was evaporated to dryness and the residue was purified by chromatography on silica, eluting with a mixture of ethyl acetate and cyclohexane with a gradient of 0-25% to give methyl 2-hydroxy-6-methoxymethylbenzoate (1.46 g) as a white crystalline solid.

Aufarbeitung

  1. temperatureheated
  2. temperatureat reflux overnight
  3. temperatureAfter cooling
  4. customevaporated to dryness
  5. customThe residue was triturated with DCM
  6. filtrationfiltered
  7. customThe filtrate was evaporated to dryness
  8. customthe residue was purified by chromatography on silica
  9. washeluting with a mixture of ethyl acetate and cyclohexane with a gradient of 0-25%

Quellen und Nachweise

ORD-Eintrag
ord-a27c6335f7d34fb3be4947c9a70e0309
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09440943B2

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