Lithium iodide → 6-(4-hydroxyphenyl)thio-2,2,3-trimethyl-2H-benzo[b]pyran

HRID 1420757

Reaktionsgleichung

Reaktionsgleichung von HRID 1420757
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([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:5][CH:4]=1.[I-].[Li+]>N1C(C)=CC(C)=CC=1C.ClCCl>[OH:2][C:3]1[CH:4]=[CH:5][C:6]([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:7][CH:8]=1

Komponenten

5

Edukt 2

HCID 66321Lithium iodide2×HCID 187828716-(4-methoxyphenyl)thio-2,2,3-trimethyl-2H-benzo[b]pyran

Produkt 1

HCID 187828866-(4-hydroxyphenyl)thio-2,2,3-trimethyl-2H-benzo[b]pyranAusbeute 77,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 79532,4,6-TrimethylpyridineLösungsmittel

Versuchsvorschrift

6-(4-Methoxyphenyl)thio-2,2,3-trimethyl-2H-benzo[b]pyran (7.816 g) (see Preparation 5) was dissolved in dry 2,4,6-collidine (30 ml), anhydrous lithium iodide (10.04 g) was added and the mixture was heated under reflux under a nitrogen atmosphere for 48 hours. A further portion of lithium iodide (9.06 g). was then added and heating was continued for another 72 hours. After cooling, the mixture was taken up in dichloromethane and washed with 2N aqueous hydrochloric acid solution (×3). The organic layer was separated, dried (anhydrous sodium sulphate), the solvent removed under reduced pressure and the residue was chromatographed on silica using dichloromethane as the eluent to yield 6-(4-hydroxyphenyl)thio-2,2,3-trimethyl-2H-benzo[b]pyran (5.799 g) as an oil.

Aufarbeitung

  1. temperaturethe mixture was heated
  2. temperatureunder reflux under a nitrogen atmosphere for 48 hours
  3. additionwas then added
  4. temperatureheating
  5. temperatureAfter cooling
  6. washwashed with 2N aqueous hydrochloric acid solution (×3)
  7. customThe organic layer was separated
  8. dry with materialdried (anhydrous sodium sulphate)
  9. customthe solvent removed under reduced pressure
  10. customthe residue was chromatographed on silica

Quellen und Nachweise

ORD-Eintrag
ord-0070bc41127a4a2bb2703635e398c548
Quelldatensatz
uspto-grants-2000_06
Patentnummer
US06071938

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