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

HRID 472973

Reaktionsgleichung

Reaktionsgleichung von HRID 472973
[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-601db6f6ccea4b8698cec5cc67d4f3bc
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08633212B2

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