Triethylamine → Methyl alpha-(4-tert-butyldimethylsilyloxy-methyl-2-n-propylphenoxy)-3,4-methylenedioxyphenylacetate

HRID 865527

Reaktionsgleichung

Reaktionsgleichung von HRID 865527
OCC1[CH:23]=[CH:22][C:6]([O:7][CH:8]([C:13]2[CH:18]=[CH:17][C:16]3[O:19][CH2:20][O:21][C:15]=3[CH:14]=2)[C:9]([O:11][CH3:12])=[O:10])=[C:5]([CH2:24][CH2:25][CH3:26])C=1.C(N([CH2:32][CH3:33])CC)C.[C:34]([Si:38]([CH3:41])([CH3:40])Cl)([CH3:37])([CH3:36])[CH3:35].C[CH2:43][O:44]C(C)=O>ClCCl.CN(C)C1C=CN=CC=1>[Si:38]([O:44][C:43]1[CH:23]=[CH:22][C:6]([O:7][CH:8]([C:13]2[CH:18]=[CH:17][C:16]3[O:19][CH2:20][O:21][C:15]=3[CH:14]=2)[C:9]([O:11][CH3:12])=[O:10])=[C:5]([CH2:24][CH2:25][CH3:26])[C:32]=1[CH3:33])([C:34]([CH3:37])([CH3:36])[CH3:35])([CH3:41])[CH3:40]

Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 28928tert-Butyldimethylsilyl chlorideHCID 19080423Methyl alpha-(4-hydroxymethyl-2-n-propyl-phenoxy)-3,4-methylenedioxyphenylacetate

Produkt 1

HCID 131719617Methyl alpha-(4-tert-butyldimethylsilyloxy-methyl-2-n-propylphenoxy)-3,4-methylenedioxyphenylacetateAusbeute 97 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 2.50 g (6.98 mmol) of the product of Step A dissolved in 20 mL of dichloromethane was added 1.95 mL (14.0 mmol) of triethylamine, 1.26 g (8.38 mmol) of tert-butyldimethylchlorosilane, 85 mg (0.1 eq) of 4-dimethylaminopyridine and the reaction mixture was stirred at room temperature for 30 minutes under a nitrogen atmosphere. The reaction was then diluted with 100 mL EtOAc, washed with water, 1.0 N HCl, saturated aqueous NaHCO3, saturated NaCl, dried (MgSO4), filtered and evaporated in vacuo to afford 3.20 g (97%) of the title compound.

Aufarbeitung

  1. washwashed with water, 1.0 N HCl, saturated aqueous NaHCO3, saturated NaCl
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. customevaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-97234efc43434420864aea725558d053
Quelldatensatz
uspto-grants-1996_10
Patentnummer
US05565485

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