Imidazole → Chloromethyl(1,1-dimethylethoxy)methyl(phenyl)silane

HRID 1980512

Reaktionsgleichung

Reaktionsgleichung von HRID 1980512
Cl[Si:2]([CH2:10][Cl:11])([CH3:9])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[C:12]([OH:16])([CH3:15])([CH3:14])[CH3:13].C(N(CC)CC)C.N1C=CN=C1>CN(C)C=O.O>[Cl:11][CH2:10][Si:2]([O:16][C:12]([CH3:15])([CH3:14])[CH3:13])([CH3:9])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Komponenten

7

Edukt 4

HCID 795ImidazoleHCID 6386tert-ButanolHCID 8471TriethylamineHCID 12418873Chloro(chloromethyl)methyl(phenyl)silane

Produkt 1

HCID 13474595Chloromethyl(1,1-dimethylethoxy)methyl(phenyl)silaneAusbeute 76,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A mixture of 15.4 g (0.075 mol) of chloro(chloromethyl)methyl(phenyl)silane, 14 ml (11.1 g, 0.15 mol) of t-butanol, 11.5 ml (8.3 g, 0.082 g) of triethylamine, and 0.5 g (0.008 mol) of imidazole in 60 ml of dimethylformamide was stirred at 80° For 2 hours. The resulting slurry was cooled, poured into 200 ml of water, and extracted with ether. The ether extracts were washed three times with water, followed by 0.1N aqueous HCl, saturated aqueous NaHCO3, and brine dried over magnesium sulfate, and evaporated to leave 14.0 g of a pale orange oil. Distillation provided 11.9 g (65%) of the title compound: bp 78°-82° (0.2 mm); nD21 1.5010; ir (neat) 3080, 3060, 2990, 2940, 1600, 1435, 1395, 1370, 1260, 1245, 1195, 1125, 1060, 1030, 815, 790, 740, 725, 705, 650 cm-1 ; nmr (CDCl3): 0.5 (3H, s), 1.3 (9H, s), 2.9 (2H, s) and 7.3-7.8 (5H, m).

Aufarbeitung

  1. temperatureThe resulting slurry was cooled
  2. extractionextracted with ether
  3. washThe ether extracts were washed three times with water
  4. dry with materialdried over magnesium sulfate
  5. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-84f386f9a72648a388f8546763acfd46
Quelldatensatz
uspto-grants-1985_04
Patentnummer
US04510136

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