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9-(t-Butyldimethylsilyloxy)-1-nonyne → 4-[9-(t-Butyldimethylsilyloxy)-1-nonynyl]4-hydroxy-7-methoxymethoxy-3-(4-methoxymethoxyphenyl)-3-methylchroman

HRID 1859292
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Reaktionsgleichung

Reaktionsgleichung von HRID 1859292
[Si:1]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]#[CH:17])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C([Li])CCC.[CH3:23][O:24][CH2:25][O:26][C:27]1[CH:48]=[CH:47][C:30]2[C:31](=[O:46])[C:32]([C:36]3[CH:41]=[CH:40][C:39]([O:42][CH2:43][O:44][CH3:45])=[CH:38][CH:37]=3)([CH3:35])[CH2:33][O:34][C:29]=2[CH:28]=1>O1CCCC1>[Si:1]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]#[C:17][C:31]1([OH:46])[C:30]2[CH:47]=[CH:48][C:27]([O:26][CH2:25][O:24][CH3:23])=[CH:28][C:29]=2[O:34][CH2:33][C:32]1([C:36]1[CH:37]=[CH:38][C:39]([O:42][CH2:43][O:44][CH3:45])=[CH:40][CH:41]=1)[CH3:35])([C:4]([CH3:5])([CH3:6])[CH3:7])([CH3:3])[CH3:2]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 140273559-(t-Butyldimethylsilyloxy)-1-nonyneHCID 154817637-Methoxymethoxy-3-(4-methoxymethoxyphenyl)-3-methylchroman-4-oneHCID 178418339Butyllithium

Produkt 1

HCID 220330974-[9-(t-Butyldimethylsilyloxy)-1-nonynyl]4-hydroxy-7-methoxymethoxy-3-(4-methoxymethoxyphenyl)-3-methylchromanAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028
Tetrahydrofuran
Lösungsmittel
2×

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

9-(t-Butyldimethylsilyloxy)-non-1-yne (0.46 g, 1.8 mmol) was dissolved in dry tetrahydrofuran (8 ml) under argon atmosphere and then cooled to -78° C. 2.5M n-Butyllithium (n-BuLi) (0.7 ml, 1.68 mmol) was slowly added dropwise thereto and then the mixture was stirred for 30 minutes. To the mixture was added dropwise 7-methoxymethyloxy-3-[4-(methoxymethyloxy)phenyl]-3-methyl-2,3-dihydro-4H-benzopyran-4-one (200 mg, 6.6 mmol) dissolved in dry tetrahydrofuran (4 ml), and then the reaction mixture was slowly warmed to room temperature. The reaction solution was quenched with water and then extracted with ethyl acetate. The organic layer was separated, dried over magnesium sulfate and concentrated. The residue was subjected to column chromatography (n-hexane:ethyl acetate=4:1) to obtain 350 mg (yield: >100%) of the title compound as a colorless oil.

Aufarbeitung

  1. temperaturethe reaction mixture was slowly warmed to room temperature
  2. customThe reaction solution was quenched with water
  3. extractionextracted with ethyl acetate
  4. customThe organic layer was separated
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-90f9d9fb21d34202b0f54bb52b27175b
Quelldatensatz
uspto-grants-2000_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06153768

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