Sodium hydride → 6'-bromo-4-methoxyspiro[cyclohexane-1,2'-inden]-1'(3'H)-one

HRID 336563

Reaktionsgleichung

Reaktionsgleichung von HRID 336563
[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH2:7][C:8]2=[O:11])=[CH:4][CH:3]=1.Br[CH2:13][CH2:14][CH:15]([O:19][CH3:20])[CH2:16][CH2:17]Br.[H-].[Na+]>C1COCC1>[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][C:7]3([CH2:17][CH2:16][CH:15]([O:19][CH3:20])[CH2:14][CH2:13]3)[C:8]2=[O:11])=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 1397781-Indanone, 6-bromo-HCID 581977301,5-Dibromo-3-methoxypentane

Produkt 1

HCID 581972636'-bromo-4-methoxyspiro[cyclohexane-1,2'-inden]-1'(3'H)-oneAusbeute 4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A mixture of 6-bromo-2,3-dihydro-1H-inden-1-one (1.037 g, 4.94 mmol) and 1,5-dibromo-3-methoxypentane (1.2 g, 4.94 mmol) in THF (16 mL) was added NaH (237.12 mg, 60%, 9.88 mmol) at room temperature. The mixture was refluxes for 3 h. The mixture was quenched with water and extracted with EtOAc. The organic layer was dried and concentrated to give the residue, which was purified by column chromatography to give 6′-bromo-4-methoxyspiro[cyclohexane-1,2′-inden]-1′(3′H)-one (60 mg, 4%).

Aufarbeitung

  1. customThe mixture was quenched with water
  2. extractionextracted with EtOAc
  3. customThe organic layer was dried
  4. concentrationconcentrated
  5. customto give the residue, which
  6. customwas purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-cdb90e2f3aba47afbf6ce8d36ab4449d
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08889703B2

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