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Dichloromethane → 4-[9-(t-Butyldimethylsilyloxy)1-nonynyl]-7-methoxy-3-(4-methoxyphenyl)-3-methylthiochroman

HRID 1859313
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1859313
ClCCl.[Si:4]([O:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][C:19]#[C:20][C:21]1(O)[C:30]2[C:25](=[CH:26][C:27]([O:31][CH3:32])=[CH:28][CH:29]=2)[S:24][CH2:23][C:22]1([C:34]1[CH:39]=[CH:38][C:37]([O:40][CH3:41])=[CH:36][CH:35]=1)[CH3:33])([C:7]([CH3:10])([CH3:9])[CH3:8])([CH3:6])[CH3:5].C([BH3-])#N.[Na+]>[I-].[Zn+2].[I-].O>[Si:4]([O:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][C:19]#[C:20][CH:21]1[C:30]2[C:25](=[CH:26][C:27]([O:31][CH3:32])=[CH:28][CH:29]=2)[S:24][CH2:23][C:22]1([C:34]1[CH:39]=[CH:38][C:37]([O:40][CH3:41])=[CH:36][CH:35]=1)[CH3:33])([C:7]([CH3:10])([CH3:9])[CH3:8])([CH3:5])[CH3:6]
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Komponenten

6

Edukt 3

HCID 6344DichloromethaneHCID 5003444Sodium cyanoborohydrideHCID 220331564-[9-(t-Butyldimethylsilyloxy)-1-nonynyl]-4-hydroxy-7-methoxy-3-(4-methoxyphenyl)-3-methylthiochroman

Produkt 1

HCID 220334284-[9-(t-Butyldimethylsilyloxy)1-nonynyl]-7-methoxy-3-(4-methoxyphenyl)-3-methylthiochromanAusbeute 62 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 9883512
zinc(II)iodide
Katalysator
HCID 962WaterLösungsmittel

Versuchsvorschrift

Dichloromethane (30 ml) was added to 4-[9-(t-butyldimethylsilyloxy)-1-nonynyl]-4-hydroxy-7-methoxy-3-(4-methoxyphenyl)-3-methylthiochroman (946 mg, 1.66 mmol) obtained in Example 27, and then zinc iodide (795 mg, 2.49 mmol) and sodium cyanoborohydride (782 mg, 12.45 mmol) were added thereto. The reaction solution was stirred for 24 hours at room temperature and, after adding water, extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified with column chromatography (n-hexane:ethyl acetate=9:1) to obtain 569 mg (yield: 62%, 3RS,4RS/3RS,4SR=5:1) of the title compound as a white solid.

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. dry with materialThe extract was dried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified with column chromatography (n-hexane:ethyl acetate=9:1)

Quellen und Nachweise

ORD-Eintrag
ord-836c12995a8f4d74b036dfc1c7176c55
Quelldatensatz
uspto-grants-2000_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06153768

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