Ethyl Acetate → 4-[9-(t-Butyldimethylsilyloxy)nonyl]-7-methoxymethoxy-3-(4-methoxymethoxyphenyl)-3-methylchroman

HRID 1792307Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1792307
[Si:1]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]#[C:17][CH:18]1[C:27]2[C:22](=[CH:23][C:24]([O:28][CH2:29][O:30][CH3:31])=[CH:25][CH:26]=2)[O:21][CH2:20][C:19]1([C:33]1[CH:38]=[CH:37][C:36]([O:39][CH2:40][O:41][CH3:42])=[CH:35][CH:34]=1)[CH3:32])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C(OCC)(=O)C>CO.O1CCCC1.[Pd]>[Si:1]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH:18]1[C:27]2[C:22](=[CH:23][C:24]([O:28][CH2:29][O:30][CH3:31])=[CH:25][CH:26]=2)[O:21][CH2:20][C:19]1([C:33]1[CH:38]=[CH:37][C:36]([O:39][CH2:40][O:41][CH3:42])=[CH:35][CH:34]=1)[CH3:32])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:2])[CH3:3]

Komponenten

6

Edukt 2

HCID 8857Ethyl AcetateHCID 220331314-[9-(t-Butyldimethylsilyloxy)-1-nonynyl]-7-methoxymethoxy-3-(4-methoxymethoxyphenyl)-3-methylchroman

Produkt 1

HCID 220330064-[9-(t-Butyldimethylsilyloxy)nonyl]-7-methoxymethoxy-3-(4-methoxymethoxyphenyl)-3-methylchromanAusbeute 8.884,4 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23938PalladiumKatalysatorHCID 887MethanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 4-[9-(t-butyldimethylsilyloxy)-1-nonynyl]-7-methoxymethoxy-3-(4-methoxymethoxyphenyl)-3-methylchroman (150 g, 2.51 mmol) in methanol (100 ml) and tetrahydrofuran (10 ml) was added 10% Pd—C (570 mg), which was then stirred at room temperature under hydrogen (atmospheric pressure) for 1 day. Ethyl acetate was added to the reaction solution, which was then filtered, extracted several times with ethyl acetate, and concentrated under reduced pressure to give the title compound (134 g, yield 89%, 3RS/4RS:3RS/4SR=6:1) as a colorless oil.

Aufarbeitung

  1. filtrationwas then filtered
  2. extractionextracted several times with ethyl acetate
  3. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-9f09e6b4c28d42718313d4fe165cf405
Quelldatensatz
uspto-grants-2006_07
Patentnummer
US07074819B2

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