Lithium iodide → 6-(3-hydroxyphenyl)thio-2,2,3-trimethyl-2H-benzo[b]pyran

HRID 1420758

Reaktionsgleichung

Reaktionsgleichung von HRID 1420758
C[O:2][C:3]1[CH:4]=[C:5]([S:9][C:10]2[CH:22]=[CH:21][C:13]3[O:14][C:15]([CH3:20])([CH3:19])[C:16]([CH3:18])=[CH:17][C:12]=3[CH:11]=2)[CH:6]=[CH:7][CH:8]=1.[I-].[Li+]>N1C(C)=CC(C)=CC=1C.ClCCl>[OH:2][C:3]1[CH:4]=[C:5]([S:9][C:10]2[CH:22]=[CH:21][C:13]3[O:14][C:15]([CH3:19])([CH3:20])[C:16]([CH3:18])=[CH:17][C:12]=3[CH:11]=2)[CH:6]=[CH:7][CH:8]=1

Komponenten

5

Edukt 2

HCID 66321Lithium iodideHCID 187828766-(3-methoxyphenyl)thio-2,2,3-trimethyl-2H-benzo[b]pyran

Produkt 1

HCID 187828646-(3-hydroxyphenyl)thio-2,2,3-trimethyl-2H-benzo[b]pyranAusbeute 67,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 79532,4,6-TrimethylpyridineLösungsmittel

Versuchsvorschrift

6-(3-Methoxyphenyl)thio-2,2,3-trimethyl-2H-benzo[b]pyran (3.5 g) (see Preparation 6) was dissolved in dry 2,4,6-collidine (15 ml), anhydrous lithium iodide (3 g) was added and the mixture was heated under reflux under a nitrogen atmosphere for 24 hours. After cooling, the mixture was taken up in dichloromethane and washed with 2N aqueous hydrochloric acid solution (×3). The-organic layer was dried (anhydrous sodium sulphate), the solvent removed under reduced pressure and the residue chromatographed on silica eluting with a solvent gradient of 1:1 hexane:dichloromethane changing to dichloromethane to yield 6-(3-hydroxyphenyl)thio-2,2,3-trimethyl-2H-benzo[b]pyran (2.25 g) as an oil.

Aufarbeitung

  1. temperaturethe mixture was heated
  2. temperatureunder reflux under a nitrogen atmosphere for 24 hours
  3. temperatureAfter cooling
  4. washwashed with 2N aqueous hydrochloric acid solution (×3)
  5. dry with materialThe-organic layer was dried (anhydrous sodium sulphate)
  6. customthe solvent removed under reduced pressure
  7. customthe residue chromatographed on silica eluting with a solvent gradient of 1:1 hexane

Quellen und Nachweise

ORD-Eintrag
ord-fd53e3dbc15b4bf1bd0df7d7492227d9
Quelldatensatz
uspto-grants-2000_06
Patentnummer
US06071938

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