p-Toluenesulfonic acid monohydrate → HCID 66815740, Verbindung

HRID 2367927Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2367927
O1CCCCC1[O:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][O:14][C:15]1[CH:16]=[C:17]([C:21]2[N:26]=[C:25]([C:27]([O:29][CH3:30])=[O:28])[CH:24]=[CH:23][CH:22]=2)[CH:18]=[CH:19][CH:20]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(OCC)(=O)C.CCCCCC>CO>[OH:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][O:14][C:15]1[CH:16]=[C:17]([C:21]2[N:26]=[C:25]([C:27]([O:29][CH3:30])=[O:28])[CH:24]=[CH:23][CH:22]=2)[CH:18]=[CH:19][CH:20]=1

Komponenten

5

Edukt 3

HCID 521998p-Toluenesulfonic acid monohydrateHCID 21226206Ethyl acetate hexaneHCID 66815652HCID 66815652, Verbindung

Produkt 1

HCID 66815740HCID 66815740, VerbindungAusbeute 65,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To a solution of methyl 6-(3-(6-(tetrahydro-2H-pyran-2-yloxy)hexyloxy)phenyl) picolinate (12), (260 mg, 0.63 mmol) in methanol (1 mL) was added catalytic p-toluenesulfonic acid monohydrate (26 mg) and the mixture was stirred at RT for 2-4 h. The reaction was monitored by TLC (ethyl acetate:hexane 1:1). After completion the volatiles were removed in vacuo and the oily residue dissolved in ethyl acetate. The solution was washed with bicarbonate and brine, dried over sodium sulfate and concentrated in vacuo. The crude product was purified by gradient flash chromatography (ethyl acetate:hexane) to provide 135 mg (65%) of 13. TLC Rf=0.34 (ethyl acetate:hexanes 1:1), MS m/z 330 (M+H)+

Aufarbeitung

  1. customAfter completion the volatiles were removed in vacuo
  2. dissolutionthe oily residue dissolved in ethyl acetate
  3. washThe solution was washed with bicarbonate and brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified by gradient flash chromatography (ethyl acetate:hexane)

Quellen und Nachweise

ORD-Eintrag
ord-032bf06ef2fc4139984137dd3474e03b
Quelldatensatz
uspto-grants-2014_04
Patentnummer
US08703700B2

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