Methyl 6-(((trifluoromethyl)sulfonyl)oxy)-1-naphthoate → HCID 66660876, Verbindung

HRID 472781

Reaktionsgleichung

Reaktionsgleichung von HRID 472781
FC(F)(F)S(O[C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[C:13]([C:17]([O:19][CH3:20])=[O:18])=[CH:12][CH:11]=[CH:10]2)(=O)=O.[CH2:23]([Mg]Br)[CH2:24][CH2:25][CH2:26][CH2:27][CH3:28]>C1COCC1.CN1C(=O)CCC1.CCOCC>[CH2:23]([C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[C:13]([C:17]([O:19][CH3:20])=[O:18])=[CH:12][CH:11]=[CH:10]2)[CH2:24][CH2:25][CH2:26][CH2:27][CH3:28]

Komponenten

6

Edukt 2

HCID 22622428Methyl 6-(((trifluoromethyl)sulfonyl)oxy)-1-naphthoateHCID 178444609HCID 178444609, Verbindung

Produkt 1

HCID 66660876HCID 66660876, VerbindungAusbeute 76 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 3283Diethyl EtherLösungsmittel2×HCID 8028TetrahydrofuranLösungsmittelHCID 13387N-methyl-2-pyrrolidoneLösungsmittel

Versuchsvorschrift

In accordance with the procedure of Furstner (Angew. Chem. Int. Ed., 2002, 41, 609-612), a solution of methyl 6-(((trifluoromethyl)sulfonyl)oxy)-1-naphthoate (334 mg, 1.0 mmol) and Fe(acac)3 in THF (6 mL) and NMP (0.56 mL) was treated with n-hexylmagnesium bromide (1.2 mL of a 2.0 M solution in Et2O, 2.4 mmol) at room temperature. After 30 min, the mixture was diluted with Et2O (20 mL) and quenched with 1 N aqueous HCl (5 mL). The phases were separated and the organic phase was washed with water (2×15 mL) and brine (15 mL), then dried (Na2SO4), filtered and concentrated in vacuo. The resulting residue was purified on 40 g silica gel (100% hexanes→20% EtOAc/hexanes, gradient) to afford 206 mg (76%) of methyl 6-hexyl-1-naphthoate.

Aufarbeitung

  1. customquenched with 1 N aqueous HCl (5 mL)
  2. customThe phases were separated
  3. washthe organic phase was washed with water (2×15 mL) and brine (15 mL)
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe resulting residue was purified on 40 g silica gel (100% hexanes→20% EtOAc/hexanes, gradient)

Quellen und Nachweise

ORD-Eintrag
ord-5a41c18c3c054799b94add1dc985435d
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08633220B2

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