Methyl Acrylate → 6'-Bromospiro[cyclohexane-1,2'-indene]-1',4(3'H)-dione

HRID 539265Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 539265
[CH3:1][C:2](C)([O-])C.[K+].[Br:7][C:8]1[CH:16]=[C:15]2[C:11]([CH2:12][CH2:13][C:14]2=[O:17])=[CH:10][CH:9]=1.[C:18]([O:22]C)(=O)[CH:19]=[CH2:20].[OH-].[K+]>C1COCC1.O>[Br:7][C:8]1[CH:16]=[C:15]2[C:11]([CH2:12][C:13]3([CH2:20][CH2:19][C:18](=[O:22])[CH2:2][CH2:1]3)[C:14]2=[O:17])=[CH:10][CH:9]=1

Komponenten

7

Edukt 4

HCID 7294Methyl AcrylateHCID 14797Potassium HydroxideHCID 1397781-Indanone, 6-bromo-HCID 23665647Potassium tert-butoxide

Produkt 1

HCID 581972056'-Bromospiro[cyclohexane-1,2'-indene]-1',4(3'H)-dioneAusbeute 72 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Potassium tert-butoxide (7.50 g, 66.81 mmol) was added in portions to 6-bromo-2,3-dihydro-1H-inden-1-one (11.75 g, 55.67 mmol) and methyl acrylate (11.05 mL, 122.5 mmol) in THF (55 mL) under cooling in an ice-bath. The mixture was stirred for 1.5 h at r.t. Water (80 mL) and KOH (3.12 g, 55.7 mmol) was added and the mixture was heated to 75° C. and then at 60° C. overnight. The mixture was cooled to 0° C., and the formed precipitate was filtered off and dried in vacuo to give the title compound (11.69 g, 72% yield). 1H NMR (500 MHz, CDCl3) δ ppm 1.83-1.92 (m, 2 H), 2.15-2.27 (m, 2 H), 2.40-2.50 (m, 2 H), 2.71 (dt, 2 H), 3.17 (s, 2 H), 7.39 (d, 1 H), 7.75 (dd, 1 H), 7.92 (d, 1 H); MS (ES+) m/z 293 [M+H]+.

Aufarbeitung

  1. temperatureunder cooling in an ice-bath
  2. temperaturethe mixture was heated to 75° C.
  3. customat 60° C.
  4. customovernight
  5. temperatureThe mixture was cooled to 0° C.
  6. filtrationthe formed precipitate was filtered off
  7. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-72ab174cbdde48b38d67d2690d9ff69f
Quelldatensatz
uspto-grants-2014_10
Patentnummer
US08865911B2

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