Pyridine → 8-(cyclopentyloxy)-7-methoxy-2-oxo-2H-chromen-4-yl 4-methylbenzenesulfonate

HRID 20627

Reaktionsgleichung

Reaktionsgleichung von HRID 20627
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8](Cl)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[CH:12]1([O:17][C:18]2[C:19]([O:30][CH3:31])=[CH:20][CH:21]=[C:22]3[C:27]=2[O:26][C:25](=[O:28])[CH:24]=[C:23]3[OH:29])[CH2:16][CH2:15][CH2:14][CH2:13]1.N1C=CC=CC=1>ClCCl>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([O:29][C:23]2[C:22]3[C:27](=[C:18]([O:17][CH:12]4[CH2:13][CH2:14][CH2:15][CH2:16]4)[C:19]([O:30][CH3:31])=[CH:20][CH:21]=3)[O:26][C:25](=[O:28])[CH:24]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 1049PyridineHCID 73974-Toluenesulfonyl chlorideHCID 771747928-(cyclopentyloxy)-4-hydroxy-7-methoxy-2H-chromen-2-one

Produkt 1

HCID 866181328-(cyclopentyloxy)-7-methoxy-2-oxo-2H-chromen-4-yl 4-methylbenzenesulfonate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

4-Methylbenzene-1-sulfonyl chloride (135 mg, 0.71 mmol) was added to a solution of 8-(cyclopentyloxy)-4-hydroxy-7-methoxy-2H-chromen-2-one (175 mg, 0.63 mmol), pyridine (0.15 mL, 1.85 mmol), and anhydrous dichloromethane (4 mL) at rt under N2. After 20 h, the reaction was concentrated and purified by silica gel chromatography (1:0→7:3; hexanes:ethyl acetate) to give 8-(cyclopentyloxy)-7-methoxy-2-oxo-2H-chromen-4-yl 4-methylbenzenesulfonate: MS (ESI): 431.3.

Aufarbeitung

  1. concentrationthe reaction was concentrated
  2. custompurified by silica gel chromatography (1:0→7:3; hexanes:ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-5723064d63964d548591af3a350eda5e
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07745646B2

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