Ammonium Chloride → 4-[6 (t-Butyldimethylsilyloxy)-1-hexynyl]-4-hydroxy-7-methoxy-3-(4-methoxyphenyl)-3-methylthiochroman

HRID 1792377Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1792377
[Si:1]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]#[CH:14])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C([Li])CCC.[CH3:20][O:21][C:22]1[CH:31]=[C:30]2[C:25]([C:26](=[O:41])[C:27]([C:33]3[CH:38]=[CH:37][C:36]([O:39][CH3:40])=[CH:35][CH:34]=3)([CH3:32])[CH2:28][S:29]2)=[CH:24][CH:23]=1.[Cl-].[NH4+]>O1CCCC1>[Si:1]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]#[C:14][C:26]1([OH:41])[C:25]2[C:30](=[CH:31][C:22]([O:21][CH3:20])=[CH:23][CH:24]=2)[S:29][CH2:28][C:27]1([C:33]1[CH:34]=[CH:35][C:36]([O:39][CH3:40])=[CH:37][CH:38]=1)[CH3:32])([C:4]([CH3:5])([CH3:6])[CH3:7])([CH3:3])[CH3:2]

Komponenten

6

Edukt 4

HCID 25517Ammonium ChlorideHCID 109799547-Methoxy-3-(4-methoxyphenyl)-3-methylthiochroman-4-oneHCID 110094486-(t-Butyldimethylsilyloxy)-1-hexyneHCID 178418339Butyllithium

Produkt 1

HCID 187702474-[6 (t-Butyldimethylsilyloxy)-1-hexynyl]-4-hydroxy-7-methoxy-3-(4-methoxyphenyl)-3-methylthiochromanAusbeute 93,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
-20 °C

Versuchsvorschrift

To a solution of 6-(t-butyldimethylsilyloxy)-1-hexyne (10.8 g, 50.9 mmol) in dry tetrahydrofiuran (100 ml) was added dropwise n-butyl lithium (30.1 ml, 48.9 mmol, 1.63M in tetrahydrofuran) at −78° C., which was then stirred at −20° C. for 1 hour. To the reaction mixture , was then added 7-methoxy-3-(4-methoxyphenyl)-3-methylthiochroman-4-one (8.0 g, 25.5 mmol) dissolved in tetrahydrofuran at −78 C for 30 min, and the resulting mixture was stirred at −10° C. (for 24 hours. After the reaction was completed, saturated ammonium chloride solution was added to the reaction solution, and the mixture was extracted with ethyl acetate. The extract was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was subjected to column chromatography (n-hexane:ethyl acetate=4:1) to give the title compound (12.5 g, yield: 93%).

Aufarbeitung

  1. stirringthe resulting mixture was stirred at −10° C. (for 24 hours
  2. extractionthe mixture was extracted with ethyl acetate
  3. dry with materialThe extract was dried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-ae864e8e07614a33b661deb59b3726e9
Quelldatensatz
uspto-grants-2006_07
Patentnummer
US07074819B2

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