Triethylamine → 3-(t-Butyldimethylsilyloxymethyl)phenyl 2-(acetyloxy)benzoate

HRID 1862537

Reaktionsgleichung

Reaktionsgleichung von HRID 1862537
[Si:1]([O:8][CH2:9][C:10]1[CH:11]=[C:12]([OH:16])[CH:13]=[CH:14][CH:15]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[C:17]([O:20][C:21]1[C:22](=[CH:26][CH:27]=[CH:28][CH:29]=1)[C:23](Cl)=[O:24])(=[O:19])[CH3:18].C(N(CC)CC)C>CCOCC.CCOC(C)=O>[C:17]([O:20][C:21]1[CH:29]=[CH:28][CH:27]=[CH:26][C:22]=1[C:23]([O:16][C:12]1[CH:13]=[CH:14][CH:15]=[C:10]([CH2:9][O:8][Si:1]([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2])[CH:11]=1)=[O:24])(=[O:19])[CH3:18]

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 796682-Acetoxybenzoyl chloride2×HCID 149405563-((((1,1-Dimethylethyl)dimethylsilyl)oxy)methyl)phenol

Produkt 1

HCID 120710543-(t-Butyldimethylsilyloxymethyl)phenyl 2-(acetyloxy)benzoateAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of Compound 3 in Et2O (120 ml) were added acetylsalicyloyl chloride (Compound 4) (5.9 g, 0.028 mol) and triethylamine (Et3N) (6.6 ml, 0.047 mol) in sequence at RT. The reaction mixture was stirred at RT under argon for 3 days. The reaction mixture was diluted with EtOAc (100 ml) and washed with aqueous saturated NaHCO3 (3×100 ml), brine (1×100 ml), and dried over anhydrous Na2SO4. The crude product obtained upon concentration was purified by column chromatography (elution solvent: 5% EtOAc in hexanes) to produce 9.4 g of Compound 5 in 100% yield.

Aufarbeitung

  1. washwashed with aqueous saturated NaHCO3 (3×100 ml), brine (1×100 ml)
  2. dry with materialdried over anhydrous Na2SO4
  3. customThe crude product obtained upon concentration
  4. customwas purified by column chromatography (elution solvent: 5% EtOAc in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-e698fe58e16d4fa2a1f2009aa22ff3b1
Quelldatensatz
uspto-grants-2003_03
Patentnummer
US06538033B2

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