4-Iodomethyl-tetrahydro-pyran-4-carboxylic acid methyl ester → Methyl 4-[(acetylsulfanyl)methyl]oxane-4-carboxylate

HRID 393690

Reaktionsgleichung

Reaktionsgleichung von HRID 393690
[CH3:1][O:2][C:3]([C:5]1([CH2:11]I)[CH2:10][CH2:9][O:8][CH2:7][CH2:6]1)=[O:4].[C:13]([O-:16])(=[S:15])[CH3:14].[K+]>CN(C)C=O.O>[CH3:1][O:2][C:3]([C:5]1([CH2:11][S:15][C:13](=[O:16])[CH3:14])[CH2:10][CH2:9][O:8][CH2:7][CH2:6]1)=[O:4]

Komponenten

5

Edukt 2

HCID 227197884-Iodomethyl-tetrahydro-pyran-4-carboxylic acid methyl esterHCID 23670855Potassium ethanethioate

Produkt 1

HCID 23448262Methyl 4-[(acetylsulfanyl)methyl]oxane-4-carboxylateAusbeute 97 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

4-Iodomethyltetrahydropyran-4-carboxylic acid methyl ester (3.05 g) was dissolved in N,N-dimethylformamide (20 ml) at room temperature and potassium thioacetate (1.47 g) added. The mixture was stirred for 18 hours then diluted with water (50 ml) and extracted with diethyl ether (4×25 ml). The combined organics were washed with saturated sodium bicarbonate solution (3×20 ml) and brine (20 ml), then dried (MgSO4), filtered and evaporated under reduced pressure to give the title compound as a yellow solid (2.42 g, 97%).

Aufarbeitung

  1. extractionextracted with diethyl ether (4×25 ml)
  2. washThe combined organics were washed with saturated sodium bicarbonate solution (3×20 ml) and brine (20 ml)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customevaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-6b47c1e01b2447308fc8e10bfe12c007
Quelldatensatz
uspto-grants-2004_10
Patentnummer
US06809100B2

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