1,7-Heptanediol → 7-Trimethylsiloxy-1-heptanol

HRID 1078994Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1078994
[CH2:1]([OH:9])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][OH:8].[H-].[Na+].[Si:12](Cl)([C:15](C)(C)C)([CH3:14])[CH3:13]>C1COCC1>[CH3:13][Si:12]([CH3:15])([CH3:14])[O:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH2:1][OH:9]

Komponenten

5

Edukt 3

HCID 123811,7-HeptanediolHCID 24758Sodium hydrideHCID 28928tert-Butyldimethylsilyl chloride

Produkt 1

HCID 189709087-Trimethylsiloxy-1-heptanol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of 1,7-heptandiol (44 mmol) in THF (15 mL) is cooled to 0° C. and treated with sodium hydride (44 mmol) followed by tert-butyldimethylsilyl chloride (44 mmol). The reaction mixture is stirred at room temperature overnight. Concentration in vacuo and flash chromatography affords 7-trimethylsiloxy-1-heptanol . To a solution of 7-trimethylsiloxy-1-heptanol (11.6 mmol) in dry dichloromethane (50 mL) is added 2,6-di-tert-butyl-4-methylpyridine (4.6 g, 22.2 mmol) and triflic anhydride (3.7 mL, 22.2 mmol) at 0° C. The reaction is stirred at room temperature for 20 min, poured into water, and extracted with dichloromethane. The combined extracts are dried over anhydrous sodium sulfate and concentrated in vacuo and to afford 7-trimethylsiloxy-1-heptyl triflate (50) which is used without further purification.

Aufarbeitung

  1. concentrationConcentration in vacuo and flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-81a4198324bd4d8dbdef6d1527d89cd4
Quelldatensatz
uspto-grants-1996_08
Patentnummer
US05550251

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