Carbon Tetrachloride → 4-chloro-8-(cyclopentyloxy)-7-methoxy-2H-chromen-2-one

HRID 20634

Reaktionsgleichung

Reaktionsgleichung von HRID 20634
[CH:1]1([O:6][C:7]2[C:8]([O:19][CH3:20])=[CH:9][CH:10]=[C:11]3[C:16]=2[O:15][C:14](=[O:17])[CH:13]=[C:12]3O)[CH2:5][CH2:4][CH2:3][CH2:2]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Cl)(Cl)(Cl)[Cl:41]>C(Cl)(Cl)Cl>[Cl:41][C:12]1[C:11]2[C:16](=[C:7]([O:6][CH:1]3[CH2:5][CH2:4][CH2:3][CH2:2]3)[C:8]([O:19][CH3:20])=[CH:9][CH:10]=2)[O:15][C:14](=[O:17])[CH:13]=1

Komponenten

5

Edukt 3

HCID 5943Carbon TetrachlorideHCID 11776TriphenylphosphineHCID 771747928-(cyclopentyloxy)-4-hydroxy-7-methoxy-2H-chromen-2-one

Produkt 1

HCID 771747944-chloro-8-(cyclopentyloxy)-7-methoxy-2H-chromen-2-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A mixture of 8-(cyclopentyloxy)-4-hydroxy-7-methoxy-2H-chromen-2-one (415 mg, 1.5 mmol, Example 1, Step 2), triphenylphosphine (787 mg, 3.0 mmol), CCl4 (0.75 mL, 7.8 mmol), and chloroform (2 mL) was heated at 80° C. in a sealed vial for 4.5 h and then allowed to cool to rt. The reaction was concentrated and purified by silica gel chromatography (1:0→4:1; hexanes:ethyl acetate) to give 4-chloro-8-(cyclopentyloxy)-7-methoxy-2H-chromen-2-one: MS (ESI): 294.8.

Aufarbeitung

  1. temperatureto cool to rt
  2. concentrationThe reaction was concentrated
  3. custompurified by silica gel chromatography (1:0→4:1; hexanes:ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-8539f12c35a34f4a8199de73e3b5f501
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07745646B2

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