Imidazole → 2,5,7-Trimethyl-2-triethylsilanyloxymethyl-6-vinyl-indan-1-ol

HRID 473071

Reaktionsgleichung

Reaktionsgleichung von HRID 473071
[OH:1][CH2:2][C:3]1([CH3:17])[CH2:11][C:10]2[C:5](=[C:6]([CH3:15])[C:7]([CH:13]=[CH2:14])=[C:8]([CH3:12])[CH:9]=2)[CH:4]1[OH:16].N1C=CN=C1.[Si:23](Cl)([CH2:28][CH3:29])([CH2:26][CH3:27])[CH2:24][CH3:25]>C(Cl)Cl.O>[CH3:17][C:3]1([CH2:2][O:1][Si:23]([CH2:28][CH3:29])([CH2:26][CH3:27])[CH2:24][CH3:25])[CH2:11][C:10]2[C:5](=[C:6]([CH3:15])[C:7]([CH:13]=[CH2:14])=[C:8]([CH3:12])[CH:9]=2)[CH:4]1[OH:16]

Komponenten

6

Edukt 3

HCID 795ImidazoleHCID 13819ChlorotriethylsilaneHCID 59415730HCID 59415730, Verbindung

Produkt 1

HCID 684751572,5,7-Trimethyl-2-triethylsilanyloxymethyl-6-vinyl-indan-1-olAusbeute 88 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To the stirred solution of starting material 7 (0.85 g, 3.66 mmol) in dry CH2Cl2 added Imidazole (0.5 g, 7.32 mmol) and TESCl (0.6 mL, 3.66 mmol) sequentially at 0° C. under argon atmosphere and stirred the reaction mixture at same temperature for 6 h. Then reaction mixture was diluted with H2O (10 mL) followed by extraction with CH2Cl2 (50 mL), brine (25 mL), dried (Na2SO4) and concentrated in vacuo. Purification by column chromatography (SiO2, 5 to 10% EtOAc in petroleum ether eluant) gave pure compound 8 (0.85 g, 88%) as syrup.

Aufarbeitung

  1. customThen reaction mixture
  2. extractionfollowed by extraction with CH2Cl2 (50 mL), brine (25 mL)
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated in vacuo
  5. customPurification by column chromatography (SiO2, 5 to 10% EtOAc in petroleum ether eluant)

Quellen und Nachweise

ORD-Eintrag
ord-16743c616dea49a9862844f9a4e5463c
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08633252B2

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