Tetrabutylammonium Fluoride → (3RS,4RS)-4-(8-hydroxyoctyl)-7-methoxy-3-(4-methoxyphenyl)-3-methylthiochroman

HRID 1792350Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1792350
[Si]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH:17]1[C:26]2[C:21](=[CH:22][C:23]([O:27][CH3:28])=[CH:24][CH:25]=2)[S:20][CH2:19][C:18]1([C:30]1[CH:35]=[CH:34][C:33]([O:36][CH3:37])=[CH:32][CH:31]=1)[CH3:29])(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[OH:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH:17]1[C:26]2[C:21](=[CH:22][C:23]([O:27][CH3:28])=[CH:24][CH:25]=2)[S:20][CH2:19][C:18]1([C:30]1[CH:35]=[CH:34][C:33]([O:36][CH3:37])=[CH:32][CH:31]=1)[CH3:29]

Komponenten

4

Edukt 2

HCID 2724141Tetrabutylammonium FluorideHCID 22033292(3RS,4RS)-4-[8-(t-Butyldimethylsilyloxy)-1-octyl]-7-methoxy-3-(4-methoxyphenyl)-3-methylthiochroman

Produkt 1

HCID 22033221(3RS,4RS)-4-(8-hydroxyoctyl)-7-methoxy-3-(4-methoxyphenyl)-3-methylthiochromanAusbeute 93 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

(3RS,4RS)-4-[8-(t-Butyldimethylsilyloxy)-1-octyl]-7-methoxy-3-(4-methoxyphenyl)-3-methylthiochroman (4.5 g, 8.29 mmol) was dissolved in tetrahydrofuran (100 ml), and cooled to 0°. To this solution was added tetrabutylammonium fluoride (16.6 ml, 16.58 mmol), and the reaction mixture was stirred at room temperature for 2 hours. The solvent was removed by evaporation under reduced pressure and the residue was dissolved in ethyl acetate, which was washed with water. The organic layer was separated, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The product was purified by column chromatography on silica gel, eluting with 30% ethyl acetate in n-hexane to afford 3.3 g of the title compound as a pale yellow oil. (yield: 93.0%)

Aufarbeitung

  1. temperaturecooled to 0°
  2. customThe solvent was removed by evaporation under reduced pressure
  3. dissolutionthe residue was dissolved in ethyl acetate
  4. washwhich was washed with water
  5. customThe organic layer was separated
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe product was purified by column chromatography on silica gel
  9. washeluting with 30% ethyl acetate in n-hexane

Quellen und Nachweise

ORD-Eintrag
ord-de0b0b87a18c4a4586ef595a0c495b2b
Quelldatensatz
uspto-grants-2006_07
Patentnummer
US07074819B2

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