Methyl iodide → HCID 66746413, Verbindung

HRID 453929Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 453929
[OH:1][C:2]1[CH:3]=[C:4]2[C:12](=[CH:13][CH:14]=1)[O:11][C:7]1([CH2:10][CH2:9][CH2:8]1)[CH2:6][C:5]2=[O:15].[C:16](=O)([O-])[O-].[K+].[K+].CI>CN(C)C=O.O>[CH3:16][O:1][C:2]1[CH:3]=[C:4]2[C:12](=[CH:13][CH:14]=1)[O:11][C:7]1([CH2:8][CH2:9][CH2:10]1)[CH2:6][C:5]2=[O:15]

Komponenten

6

Edukt 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 667463336-Hydroxyspiro[2H-1-benzopyran-2,1′-cyclobutan]-4(3H)-one

Produkt 1

HCID 66746413HCID 66746413, VerbindungAusbeute 95 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To the stirred solution of 6-hydroxyspiro[chromene-2,1′-cyclobutan]-4-(3H)-one (8 g, 39.215 mmol) in dry dimethylformamide (150 ml), potassium carbonate (16.28 g, 117.64 mmol) and methyl iodide (4.88 ml, 78.431 mmol) were added and the reaction mixture was stirred at room temperature under nitrogen atmosphere for 2 h. After the completion of the reaction, the reaction mixture was diluted with water (100 ml), extracted with ethyl acetate (3×300 ml), the combined organic layers washed with water (3×100 ml), brine (60 ml), dried (Na2SO4), filtered and concentrated to yield 8.13 g of the product; 1H NMR (300 MHz, CDCl3) δ 1.67-1.77 (m, 1H), 1.85-1.97 (m, 1H), 2.11-2.18 (m, 2H), 2.23-2.34 (m, 2H), 2.87 (s, 2H), 3.77 (s, 3H), 6.88 (d, J=9.6 Hz, 1H), 7.06 (d, J=8.7 Hz, 1H), 7.25 (s, 1H).

Aufarbeitung

  1. customAfter the completion of the reaction
  2. extractionextracted with ethyl acetate (3×300 ml)
  3. washthe combined organic layers washed with water (3×100 ml), brine (60 ml)
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-6335513ff27f4e8fae80d9a231fc799c
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08492568B2

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