2-Dimethylaminopyridine → 2,2-Dimethyl-4-[(1-oxodecyl)oxy]butanoic acid phenylmethyl ester

HRID 569505Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 569505
[C:1]1([CH2:7][O:8][C:9](=[O:16])[C:10]([CH3:15])([CH3:14])[CH2:11][CH2:12][OH:13])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CN(C1C=CC=CN=1)C.[C:26](Cl)(=[O:36])[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35]>ClCCl>[C:1]1([CH2:7][O:8][C:9](=[O:16])[C:10]([CH3:14])([CH3:15])[CH2:11][CH2:12][O:13][C:26](=[O:36])[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Komponenten

5

Edukt 3

HCID 218852-DimethylaminopyridineHCID 66982Decanoyl chlorideHCID 141523044-Hydroxy-2,2-dimethyl-butyric acid benzyl ester

Produkt 1

HCID 141523052,2-Dimethyl-4-[(1-oxodecyl)oxy]butanoic acid phenylmethyl esterAusbeute 74,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a solution of 4-hydroxy-2,2-dimethylbutanoic acid phenylmethyl ester (1.11 g), in dichloromethane in an ice bath, was added dimethylaminopyridine (0.72 g) followed by a solution of decanoyl chloride (0.95 g) in dichloromethane (5 mL). The mixture was stirred at room temperature for 2 hours and was filtered. The filtrate was evaporated and the residue was chromatographed on silica gel eluting with dichloromethane to afford 1.4 g (74.5%) of 2,2-dimethyl-4-[(1-oxodecyl)oxy]butanoic acid phenylmethyl ester. A portion was evaporatively distilled to give an analytical sample as a colorless oil: bp 190° C./0.15 mm; IR (CHCl3) 1720 (C=O) and 697 cm-1 (Ph); NMR (CDCl3) δ 0.87 (t, 3, CH3), 1.25-1.60 (m, 20, CH2 and CH3), 1.93 (t, 2, CH2), 2.23 (t, 2, CH2), 4.11 (t, 2, CH 2), 5.11 (s, 2, CH2) and 7.33 (s, 5, Ph); MS m/e 376 and 91.

Aufarbeitung

  1. filtrationwas filtered
  2. customThe filtrate was evaporated
  3. customthe residue was chromatographed on silica gel eluting with dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-7db00ab9ab694dc89c9cc7f64c2f559c
Quelldatensatz
uspto-grants-1988_03
Patentnummer
US04732902

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