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Ammonium Chloride → 2-t-Butyldimethylsilyloxymethyl-6-hydroxymethylnaphthalene

HRID 348732
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 348732
[OH:1][CH2:2][C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[C:8]([CH2:13][OH:14])[CH:9]=2)[CH:4]=1.[Si:15](Cl)([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:17])[CH3:16].[Cl-].[NH4+]>CN(C=O)C.N1C=CN=C1>[Si:15]([O:1][CH2:2][C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[C:8]([CH2:13][OH:14])[CH:9]=2)[CH:4]=1)([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:17])[CH3:16]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 25517Ammonium ChlorideHCID 28928tert-Butyldimethylsilyl chlorideHCID 117887222,6-Bis(hydroxymethyl)naphthalene

Produkt 1

HCID 230792982-t-Butyldimethylsilyloxymethyl-6-hydroxymethylnaphthaleneAusbeute 48,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 795ImidazoleLösungsmittel
HCID 6228
Dimethylformamide
Lösungsmittel
2×

Versuchsvorschrift

The compound (3.41 g) obtained in Example 121-1 was dissolved in anhydrous DMF (200 ml). Then, t-butyldimethylsilyl chloride (2.73 g) dissolved in imidazole (1.48 g) and anhydrous DMF (50 ml) was dropped in this solution, and the whole was stirred overnight at room temperature. After completion of the reaction, the solution was added with a saturated aqueous ammonium chloride solution and stirred. The solution was extracted with chloroform and the extract was then washed with a saturated aqueous sodium bicarbonate solution, a saturated aqueous ammonium chloride solution, and saturated saline solution. Then, the organic layer was dried with anhydrous sodium sulfate. Subsequently, the solvent was distilled off and the residue was then purified through silica gel column chromatography (chloroform), thereby obtaining the subject compound (2.68 g) as a white solid.

Aufarbeitung

  1. customAfter completion of the reaction
  2. stirringstirred
  3. extractionThe solution was extracted with chloroform
  4. washthe extract was then washed with a saturated aqueous sodium bicarbonate solution
  5. dry with materialThen, the organic layer was dried with anhydrous sodium sulfate
  6. distillationSubsequently, the solvent was distilled off
  7. customthe residue was then purified through silica gel column chromatography (chloroform)

Quellen und Nachweise

ORD-Eintrag
ord-4bb6032d1e7d427c89924089d62dcd73
Quelldatensatz
uspto-grants-2007_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07176227B2

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