Triisopropylsilyl chloride → HCID 86758594, Verbindung

HRID 1017677Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1017677
[OH:1][C:2]1([OH:14])[CH:7]=[CH:6][CH:5]=[C:4]([CH2:8][N:9]2[CH2:13][CH2:12][CH2:11][CH2:10]2)[CH2:3]1.[CH:15](N(C(C)C)CCCC)([CH3:17])[CH3:16].[CH:26]([Si:29](Cl)([CH:33]([CH3:35])[CH3:34])[CH:30]([CH3:32])[CH3:31])([CH3:28])[CH3:27]>CN(C)C=O>[CH2:17]([O:14][C:2]1([O:1][Si:29]([CH:33]([CH3:35])[CH3:34])([CH:30]([CH3:32])[CH3:31])[CH:26]([CH3:28])[CH3:27])[CH:7]=[CH:6][CH:5]=[C:4]([CH2:8][N:9]2[CH2:10][CH2:11][CH2:12][CH2:13]2)[CH2:3]1)[C:15]#[CH:16]

Komponenten

5

Edukt 3

HCID 139400Triisopropylsilyl chlorideHCID 11062646N,N-DiisopropylbutylamineHCID 18403794HCID 18403794, Verbindung

Produkt 1

HCID 86758594HCID 86758594, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 3-hydroxy-1-(pyrrolidin-1-yl)methyl-3-hydroxybenzene (0.95 g) in dry dimethylformamide (5 ml) was added by syringe, with stirring, diisopropylbutylamine (1.1 ml) followed by triisopropylsilyl chloride (0.97 ml). The reaction mixture was stirred at ambient temperature for 1 hr, ice (10 g) was added and after stirring for 10 mins, the mixture was poured into ice/water and extracted with ethyl acetate. The extract was washed with water, saturated sodium chloride solution, dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated. The residue was flash column chromatographed (silica gel) eluting with dichloromethane, 1%, 2% and 5% methanol/dichloromethane. The appropriate fractions were collected and concentrated to give 0.65 g of product. Additional fractions were collected, concentrated and chromatographed over silica gel. Concentration of the appropriate fractions gave 0.15 g of product. Total yield 0.80 g (50%).

Aufarbeitung

  1. stirringThe reaction mixture was stirred at ambient temperature for 1 hr
  2. stirringafter stirring for 10 mins
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with water, saturated sodium chloride solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationthe filtrate was concentrated
  8. customchromatographed (silica gel)
  9. washeluting with dichloromethane, 1%, 2% and 5% methanol/dichloromethane
  10. customThe appropriate fractions were collected
  11. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-33e619dc0963441cb3bc327b48e5e7a1
Quelldatensatz
uspto-grants-2002_11
Patentnummer
US06479495B1

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