Sodium Chloride → 2,6-Dichloro-4-[3-((tert-butyldimethylsilanyloxy))-2-(tert-butyldimethylsilanyloxymethyl)-propoxy)-benzaldehyde

HRID 496651Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 496651
[Cl:1][C:2]1[CH:9]=[C:8]([OH:10])[CH:7]=[C:6]([Cl:11])[C:3]=1[CH:4]=[O:5].[Si:12]([O:19][CH2:20][CH:21]([CH2:28][O:29][Si:30]([C:33]([CH3:36])([CH3:35])[CH3:34])([CH3:32])[CH3:31])[CH2:22]OS(C)(=O)=O)([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:14])[CH3:13].C(=O)([O-])[O-].[K+].[K+].C1OCCOCCOCCOCCOCCOC1.[Na+].[Cl-]>CN(C)C=O.C(OCC)(=O)C>[Cl:1][C:2]1[CH:9]=[C:8]([O:10][CH2:22][CH:21]([CH2:28][O:29][Si:30]([C:33]([CH3:34])([CH3:36])[CH3:35])([CH3:31])[CH3:32])[CH2:20][O:19][Si:12]([C:15]([CH3:16])([CH3:17])[CH3:18])([CH3:13])[CH3:14])[CH:7]=[C:6]([Cl:11])[C:3]=1[CH:4]=[O:5]

Komponenten

8

Edukt 5

HCID 5234Sodium ChlorideHCID 11430Potassium CarbonateHCID 2855718-Crown-6HCID 5283822,6-Dichloro-4-hydroxybenzaldehydeHCID 11015147Methanesulfonic acid 3-(tert-butyldimethylsilanyloxy)-2-(tert-butyldimethylsilanyloxymethyl)propyl ester

Produkt 1

HCID 1317245862,6-Dichloro-4-[3-((tert-butyldimethylsilanyloxy))-2-(tert-butyldimethylsilanyloxymethyl)-propoxy)-benzaldehyde

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

3.43 g (18 mmol) A1, 7.40 g (18 mmol) methanesulfonic acid 3-(tert-butyldimethylsilanyloxy)-2-(tert-butyldimethylsilanyloxymethyl)propyl ester (Kim, H. S., et al., J. Med. Chem. 44 (2001) 3092-3108), 3.72 g (27 mmol) potassium carbonate and 41 mg (0.15 mmol) 18-crown-6 were stirred in 40 ml dimethylformamide at 40° C. overnight. 600 ml ethyl acetate and 250 ml aqueous NaCl were added. The organic layer was washed four times with saturated aqueous NaCl (80 ml each), dried over sodium sulfate and evaporated to dryness. Column chromatography of the residue on SiGel (heptane/ethyl acetate 10:1) yielded 508 mg (27%) A26.

Aufarbeitung

  1. washThe organic layer was washed four times with saturated aqueous NaCl (80 ml each)
  2. dry with materialdried over sodium sulfate
  3. customevaporated to dryness
  4. customColumn chromatography of the residue on SiGel (heptane/ethyl acetate 10:1) yielded 508 mg (27%) A26

Quellen und Nachweise

ORD-Eintrag
ord-35dc0fedf083469dad140a03cd22b4b2
Quelldatensatz
uspto-grants-2005_09
Patentnummer
US06946471B2

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