Tetraethylene Glycol → 13,13,14,14-Tetramethyl-3,6,9,12-tetraoxa-13-silapentadecan-1-ol

HRID 1257951Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1257951
[CH2:1]([OH:13])[CH2:2][O:3][CH2:4][CH2:5][O:6][CH2:7][CH2:8][O:9][CH2:10][CH2:11][OH:12].[CH3:14][C:15]([Si:18](Cl)([CH3:20])[CH3:19])([CH3:17])[CH3:16].C(N(CC)CC)C>ClCCl>[C:15]([Si:18]([CH3:20])([CH3:19])[O:12][CH2:11][CH2:10][O:9][CH2:8][CH2:7][O:6][CH2:5][CH2:4][O:3][CH2:2][CH2:1][OH:13])([CH3:17])([CH3:16])[CH3:14]

Komponenten

5

Edukt 3

HCID 8200Tetraethylene GlycolHCID 8471TriethylamineHCID 28928tert-Butyldimethylsilyl chloride

Produkt 1

HCID 1482766913,13,14,14-Tetramethyl-3,6,9,12-tetraoxa-13-silapentadecan-1-olAusbeute 42 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Tetraethylene glycol, 4c (1.12 g, 5.77 mmol) and TBDMSCl (0.87 g, 5.77 mmol) were dissolved in dichloromethane (25 ml) followed by triethyl amine (1.46 g, 14.4 mmol). The solution was stirred at room temperature for 2 hours. After standard workup with dichloromethane, the residue was purified by silica gel column chromatography (50% ethyl acetate in hexane) to afford 5c (744 mg, 42%): 1H NMR δ 3.66 (m, 16H), 2.51 (t, 1H, J=5.86 Hz), 0.89 (s, 9H), 0.07 (s, 6H).

Aufarbeitung

  1. customAfter standard workup with dichloromethane, the residue was purified by silica gel column chromatography (50% ethyl acetate in hexane)

Quellen und Nachweise

ORD-Eintrag
ord-4ae5757e001444ac823aa4bfccfb6f48
Quelldatensatz
uspto-grants-2013_06
Patentnummer
US08465726B2

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