Sodium Thiosulfate Pentahydrate → methyl 3-hydroxy-5-[(1S)-2-hydroxy-1-methylethoxy]benzoate

HRID 20524

Reaktionsgleichung

Reaktionsgleichung von HRID 20524
C[Si](I)(C)C.[OH:6][C:7]1[CH:8]=[C:9]([CH:14]=[C:15]([O:17][C@@H:18]([CH3:22])[CH2:19][O:20]C)[CH:16]=1)[C:10]([O:12][CH3:13])=[O:11].O.O.O.O.O.S([O-])([O-])(=O)=S.[Na+].[Na+].C(=O)(O)[O-].[Na+]>C(#N)C.CO>[OH:6][C:7]1[CH:8]=[C:9]([CH:14]=[C:15]([O:17][C@@H:18]([CH3:22])[CH2:19][OH:20])[CH:16]=1)[C:10]([O:12][CH3:13])=[O:11]

Komponenten

7

Edukt 4

HCID 61475Sodium Thiosulfate PentahydrateHCID 85247Trimethylsilyl iodideHCID 516892Sodium BicarbonateHCID 59127146methyl 3-hydroxy-5-[(1S)-2-methoxy-1-methylethoxy]benzoate

Produkt 1

HCID 59127187methyl 3-hydroxy-5-[(1S)-2-hydroxy-1-methylethoxy]benzoateAusbeute 47 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

Trimethylsilyl iodide (115 mL, 0.79 mol) was added to a solution of methyl 3-hydroxy-5-[(1S)-2-methoxy-(1-methylethyl)oxy]benzoate (38.01 g, 0.158 mol) in acetonitrile (500 mL) and stirred for 24 hours. Methanol (300 mL) was added and the reaction stirred for 10 mins. 10% w/v Aqueous sodium thiosulfate pentahydrate (100 mL) was added to the mixture and stirred for 20 mins. The reaction mixture was neutralised with saturated aqueous sodium bicarbonate solution, the organic solvents removed in vacuo, and the product extracted into ethyl acetate (4×100 mL). The combined organic layers were dried (MgSO4), filtered and the solvents removed in vacuo. The crude material was crystallised from ethyl acetate to give the title compound (16.80 g)

Aufarbeitung

  1. stirringthe reaction stirred for 10 mins
  2. additionwas added to the mixture
  3. stirringstirred for 20 mins
  4. customthe organic solvents removed in vacuo
  5. extractionthe product extracted into ethyl acetate (4×100 mL)
  6. dry with materialThe combined organic layers were dried (MgSO4)
  7. filtrationfiltered
  8. customthe solvents removed in vacuo
  9. customThe crude material was crystallised from ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-c13cbd53a2484403be1275b169a3f48d
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07745475B2

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