Dimethylformamide → (R)-tert-butyldimethyl(1-methylcyclohex-2-enyloxy)silane

HRID 74980Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 74980
[CH3:1][C@@:2]1([OH:8])[CH2:7][CH2:6][CH2:5][CH:4]=[CH:3]1.CN(C=O)C.N1C=NCC=1.[C:19]([Si:23]([CH3:26])([CH3:25])Cl)([CH3:22])([CH3:21])[CH3:20]>CN(C)C1C=CN=CC=1.CCOCC>[C:19]([Si:23]([CH3:26])([CH3:25])[O:8][C@:2]1([CH3:1])[CH2:7][CH2:6][CH2:5][CH:4]=[CH:3]1)([CH3:22])([CH3:21])[CH3:20]

Komponenten

7

Edukt 4

HCID 6228DimethylformamideHCID 28928tert-Butyldimethylsilyl chlorideHCID 11094567(R)-1-methylcyclohex-2-enol2×HCID 127446564H-Imidazole

Produkt 1

HCID 68008146(R)-tert-butyldimethyl(1-methylcyclohex-2-enyloxy)silane

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

To a solution of (R)-1-methylcyclohex-2-enol, 50a, (1.00 g, 8.91 mmol) in 20 dry DMF at room temperature was added 4H-imidazole (1.82 g, 26.74 mmol), tert-butyldimethylchlorosilane (2.02 g, 13.33 mmol) and a catalytic amount of 4-dimethylaminopyridine (0.11 g, 0.89 mmol). The resulting mixture was stirred at room temperature overnight. It was then diluted with ether, washed consecutively with water, citric acid and water. The organic phase was dried with MgSO4, filtered and concentrated in vacuo. The colorless crude oil 1.98 g was used directly in the next step without further purification.

Aufarbeitung

  1. washwashed consecutively with water, citric acid and water
  2. dry with materialThe organic phase was dried with MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe colorless crude oil 1.98 g was used directly in the next step without further purification

Quellen und Nachweise

ORD-Eintrag
ord-d8e9a94d9dc5491ba892b5f4ccd25b07
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08829007B2

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