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Tetrahydrofuran → (3RS,4RS)-4-(4-hydroxyphenyl)-7-methoxymethyloxy-3-[4-(methoxymethyloxy)phenyl]-3-methylthiochroman

HRID 1859342
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1859342
O1CCCC1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[Si]([O:31][C:32]1[CH:37]=[CH:36][C:35]([CH:38]2[C:47]3[C:42](=[CH:43][C:44]([O:48][CH2:49][O:50][CH3:51])=[CH:45][CH:46]=3)[S:41][CH2:40][C:39]2([C:53]2[CH:58]=[CH:57][C:56]([O:59][CH2:60][O:61][CH3:62])=[CH:55][CH:54]=2)[CH3:52])=[CH:34][CH:33]=1)(C(C)(C)C)(C)C>O>[OH:31][C:32]1[CH:37]=[CH:36][C:35]([CH:38]2[C:47]3[C:42](=[CH:43][C:44]([O:48][CH2:49][O:50][CH3:51])=[CH:45][CH:46]=3)[S:41][CH2:40][C:39]2([C:53]2[CH:54]=[CH:55][C:56]([O:59][CH2:60][O:61][CH3:62])=[CH:57][CH:58]=2)[CH3:52])=[CH:34][CH:33]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 8028Tetrahydrofuran2×HCID 2724141Tetrabutylammonium FluorideHCID 17871376(3RS,4RS)-4-(4-t-butyldimethylsilyloxyphenyl)-7-methoxymethyloxy-3-[4-(methoxymethyloxy)phenyl]-3-methylthiochroman

Produkt 1

HCID 22123581(3RS,4RS)-4-(4-hydroxyphenyl)-7-methoxymethyloxy-3-[4-(methoxymethyloxy)phenyl]-3-methylthiochromanAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

Under argon atmosphere, tetrahydrofuran solution of tetrabutylammonium fluoride (1.0M, 2.27 ml, 2.27 mmol) was added dropwise to tetrahydrofuran solution (35 ml) of (3RS,4RS)-4-(4-t-butyldimethylsilyloxyphenyl)-7-methoxymethyloxy-3-[4-(methoxymethyloxy)phenyl]-3-methylthiochroman (856 mg, 1.51 mmol) at 0° C. and the resulting mixture was stirred for 2 hours. After adding water, the reaction solution was extracted with ethyl acetate. The organic layer was washed with saturated saline, dried over anhydrous magnesium sulfate and then distilled under reduced pressure to remove the solvent. The crude product thus obtained was purified with silica gel column chromatography (ethyl acetate:hexane=1:2) to obtain 682 mg (yield: 100%) of the title compound.

Aufarbeitung

  1. extractionthe reaction solution was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated saline
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationdistilled under reduced pressure
  5. customto remove the solvent
  6. customThe crude product thus obtained
  7. customwas purified with silica gel column chromatography (ethyl acetate:hexane=1:2)

Quellen und Nachweise

ORD-Eintrag
ord-607a79ef86d8467d8c66b562d65309a5
Quelldatensatz
uspto-grants-2000_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06153768

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