Sodium bis(trimethylsilyl)amide → 4-((3-(4-Chlorophenoxy)propylsulfanyl)methyl)-tetrahydropyran-4-carboxylic Acid

HRID 1840509Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1840509
C([S:4][CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][CH:10]=1)(=O)C.C[Si](C)(C)[N-][Si](C)(C)C.[Na+].[C:26]1(=[O:35])[C:29]2([CH2:34][CH2:33][O:32][CH2:31][CH2:30]2)[CH2:28][O:27]1>CO>[Cl:15][C:12]1[CH:13]=[CH:14][C:9]([O:8][CH2:7][CH2:6][CH2:5][S:4][CH2:28][C:29]2([C:26]([OH:27])=[O:35])[CH2:34][CH2:33][O:32][CH2:31][CH2:30]2)=[CH:10][CH:11]=1

Komponenten

5

Edukt 3

HCID 2724254Sodium bis(trimethylsilyl)amideHCID 155411872,7-Dioxaspiro[3.5]nonan-1-oneHCID 234482731-Acetylsulfanyl-3-(4-chlorophenoxy)propane

Produkt 1

HCID 98845604-((3-(4-Chlorophenoxy)propylsulfanyl)methyl)-tetrahydropyran-4-carboxylic AcidAusbeute 10,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel2×

Versuchsvorschrift

A solution of Intermediate 3 (0.80 g) in methanol was treated with a solution of sodium hexamethyldisilazide (1 M in THF, 3.3 ml) at 0° C. and the resulting mixture was stirred for 2 h, then a solution of Intermediate 1 (460 mg) in methanol was added. The mixture was stirred for 18 h, then evaporated and the residue dissolved in water and washed with diethyl ether. The aqueous phase was acidified with citric acid and extracted with dichloromethane; the organic layer was then washed with brine, dried over MgSO4 and evaporated to give the title compound (0.12 g) as a colourless oil.

Aufarbeitung

  1. stirringThe mixture was stirred for 18 h
  2. customevaporated
  3. dissolutionthe residue dissolved in water
  4. washwashed with diethyl ether
  5. extractionextracted with dichloromethane
  6. washthe organic layer was then washed with brine
  7. dry with materialdried over MgSO4
  8. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-a0122586262d4a25adf0a64f4a296565
Quelldatensatz
uspto-grants-2004_01
Patentnummer
US06680338B2

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