Chlorotrimethylsilane → 1-(3-Oxo-2,6,6-trimethyl-1-cyclohexen-1-yl)-3-methyl-3-trimethylsiloxy-1,4-pentadiene

HRID 374353Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 374353
[O:1]=[C:2]1[CH2:7][CH2:6][C:5]([CH3:9])([CH3:8])[C:4]([CH:10]=[CH:11][C:12]([CH3:16])([OH:15])[CH:13]=[CH2:14])=[C:3]1[CH3:17].C(N(CC)CC)C.[CH3:25][Si:26]([CH3:29])([CH3:28])Cl>C(Cl)Cl.CN(C1C=CN=CC=1)C>[O:1]=[C:2]1[CH2:7][CH2:6][C:5]([CH3:8])([CH3:9])[C:4]([CH:10]=[CH:11][C:12]([CH3:16])([O:15][Si:26]([CH3:29])([CH3:28])[CH3:25])[CH:13]=[CH2:14])=[C:3]1[CH3:17]

Komponenten

6

Edukt 3

HCID 6397ChlorotrimethylsilaneHCID 8471TriethylamineHCID 54402789HCID 54402789, Verbindung

Produkt 1

HCID 539472351-(3-Oxo-2,6,6-trimethyl-1-cyclohexen-1-yl)-3-methyl-3-trimethylsiloxy-1,4-pentadiene

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of 1-(3-oxo-2,6,6-trimethyl-1-cyclohexen-1-yl)-3-methyl-1,4-pentadiene-3-ol (2.34 g, 10 mmoles)(prepared as described in J. Org. Chem. 47, 2130-2134 (1982)) in methylenechloride is added triethylamine (2.08 ml, 15 mmoles), trimethylchlorosilane (1.9 ml, 15 mmoles), and N,N-dimethyl-4-aminopyridine (5 mg, catalytic amount). The mixture is stirred at room temperature for four hours, followed by concentration in vacuo and trituration with dry diethylether. The suspension is filtered and the filtrate is concentrated in vacuo yielding the title compound as a slightly yellow oil.

Aufarbeitung

  1. concentrationfollowed by concentration in vacuo and trituration with dry diethylether
  2. filtrationThe suspension is filtered
  3. concentrationthe filtrate is concentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-5525cab653b940ecb1bbd615f6e94256
Quelldatensatz
uspto-grants-1992_11
Patentnummer
US05166441

Notizen zur Reaktion

Wird geladen…