Methyl iodide → Methyl 4-(1,4-dioxaspiro[4.5]dec-7-en-8-yl)benzoate

HRID 1443419Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1443419
[O:1]1[C:5]2([CH2:10][CH2:9][C:8]([C:11]3[CH:19]=[CH:18][C:14]([C:15]([OH:17])=[O:16])=[CH:13][CH:12]=3)=[CH:7][CH2:6]2)[O:4][CH2:3][CH2:2]1.IC.[C:22](=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C.O>[O:1]1[C:5]2([CH2:10][CH2:9][C:8]([C:11]3[CH:12]=[CH:13][C:14]([C:15]([O:17][CH3:22])=[O:16])=[CH:18][CH:19]=3)=[CH:7][CH2:6]2)[O:4][CH2:3][CH2:2]1

Komponenten

6

Edukt 3

HCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 595560954-(1,4-Dioxaspiro[4.5]dec-7-en-8-yl)benzoic acid

Produkt 1

HCID 22730331Methyl 4-(1,4-dioxaspiro[4.5]dec-7-en-8-yl)benzoateAusbeute 72 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A mixture of 4-(1,4-dioxaspiro[4.5]dec-7-en-8-yl)benzoic acid (572 mg, 2.20 mmol), iodomethane (140 μL, 2.24 mmol), and cesium carbonate (710 mg, 2.17 mmol) in 6 mL of DMF was stirred at rt for 16 h. The mixture was diluted with H2O (10 mL) and extracted with Et2O (100 mL). The organic layer was separated, dried over MgSO4, and concentrated. Chromatography on a Biotage 40S cartridge using 3:17 v/v EtOAc/hexanes as the eluant afforded 399 mg (72%) of the title compound.

Aufarbeitung

  1. extractionextracted with Et2O (100 mL)
  2. customThe organic layer was separated
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-dbc79623aa6c48939795b3758fb1fa55
Quelldatensatz
uspto-grants-2010_02
Patentnummer
US07659294B2

Notizen zur Reaktion

Wird geladen…