Sodium methanethiolate → 1-(2-Hydroxyphenyl)-4-methyl-1-(3-methyl-2-pyridyl)-2-buten-1-ol

HRID 892510

Reaktionsgleichung

Reaktionsgleichung von HRID 892510
C[O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]([C:15]1[C:20]([CH3:21])=[CH:19][CH:18]=[CH:17][N:16]=1)([OH:14])[CH:10]=[C:11]([CH3:13])C.[CH3:22][S-].[Na+]>CN(C)C=O>[OH:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]([C:15]1[C:20]([CH3:21])=[CH:19][CH:18]=[CH:17][N:16]=1)([OH:14])[CH:10]=[CH:11][CH2:13][CH3:22]

Komponenten

4

Edukt 2

HCID 4378561Sodium methanethiolateHCID 198956601-(2-Methoxyphenyl)-3-methyl-1-(3-methyl-2-pyridyl)-2-buten-1-ol

Produkt 1

HCID 545243991-(2-Hydroxyphenyl)-4-methyl-1-(3-methyl-2-pyridyl)-2-buten-1-olAusbeute 66,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

7.13 g of 1-(2-methoxyphenyl)-3-methyl-1-(3-methyl-2-pyridyl)-2-buten-1-ol were dissolved in 100 ml of dimethylformamide at room temperature and 5.29 g of sodium methanethiolate were added. After stirring at 120° C. for 2 hours the mixture was allowed to cool to room temperature and then evaporated. Water and ethyl acetate were added, and the organic phase was separated, dried over sodium sulphate and evaporated. The residue was chromatographed on silica gel using ethyl acetate/petroleum ether (1:4) for the elution. There were obtained 4.53 g of 1-(2-hydroxyphenyl)-4-methyl-1-(3-methyl-2-pyridyl)-2-buten-1-ol in the form of an oil.

Aufarbeitung

  1. temperatureto cool to room temperature
  2. customevaporated
  3. additionWater and ethyl acetate were added
  4. customthe organic phase was separated
  5. dry with materialdried over sodium sulphate
  6. customevaporated
  7. customThe residue was chromatographed on silica gel
  8. washfor the elution

Quellen und Nachweise

ORD-Eintrag
ord-261495a6734b439388bd3208fcfde01b
Quelldatensatz
uspto-grants-1992_06
Patentnummer
US05118694

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