Triethylamine → Methyl 4-({5-[(methylsulfonyl)oxy]pentyl}oxy)benzoate

HRID 68642Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 68642
[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][O:7][C:8]1[CH:17]=[CH:16][C:11]([C:12]([O:14][CH3:15])=[O:13])=[CH:10][CH:9]=1.C(N(CC)CC)C.[CH3:25][S:26](Cl)(=[O:28])=[O:27]>C(OCC)(=O)C>[CH3:25][S:26]([O:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][O:7][C:8]1[CH:9]=[CH:10][C:11]([C:12]([O:14][CH3:15])=[O:13])=[CH:16][CH:17]=1)(=[O:28])=[O:27]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 65019122Methyl 4-((5-hydroxypentyl)oxy)benzoate

Produkt 1

HCID 86225473Methyl 4-({5-[(methylsulfonyl)oxy]pentyl}oxy)benzoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel2×

Versuchsvorschrift

To a solution of the compound 24 (3.58 g) and triethylamine (2.76 mL) in ethyl acetate (50 mL), methanesulfonyl chloride (0.78 mL) was slowly added under ice cooling. The reaction mixture was stirred under ice cooling for 2 hours. The reaction mixture was diluted with ethyl acetate (100 mL). The diluted solution was washed in turn with water and saturated brine, dried over anhydrous magnesium sulfate and then concentrated. The residue was purified by silica gel chromatography (ethyl acetate:methanol=1:0→10:1) to obtain the title compound (3.70 g) having the following physical properties.

Aufarbeitung

  1. washThe diluted solution was washed in turn with water and saturated brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationconcentrated
  4. customThe residue was purified by silica gel chromatography (ethyl acetate:methanol=1:0→10:1)

Quellen und Nachweise

ORD-Eintrag
ord-50f02411b4ae4fe5a4fce6a15e60da15
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08822459B2

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