1,2-Dimethoxyethane → 3-(3,5,5,8,8-Pentamethyl-5,6,7,8-tetrahydro-2-naphthyl)benzaldehyde

HRID 2417321Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2417321
COCCOC.Br[C:8]1[CH:9]=[C:10]([CH:13]=[CH:14][CH:15]=1)[CH:11]=[O:12].[CH3:16][C:17]1[C:18](B(O)O)=[CH:19][C:20]2[C:21]([CH3:30])([CH3:29])[CH2:22][CH2:23][C:24]([CH3:28])([CH3:27])[C:25]=2[CH:26]=1.C(=O)([O-])[O-].[K+].[K+]>C(O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:16][C:17]1[C:18]([C:8]2[CH:9]=[C:10]([CH:13]=[CH:14][CH:15]=2)[CH:11]=[O:12])=[CH:19][C:20]2[C:21]([CH3:30])([CH3:29])[CH2:22][CH2:23][C:24]([CH3:28])([CH3:27])[C:25]=2[CH:26]=1

Komponenten

7

Edukt 4

HCID 80711,2-DimethoxyethaneHCID 11430Potassium CarbonateHCID 765833-BromobenzaldehydeHCID 10037535(3,5,5,8,8-Pentamethyl-5,6,7,8-tetrahydronaphthalen-2-yl)boronic acid

Produkt 1

HCID 223455053-(3,5,5,8,8-Pentamethyl-5,6,7,8-tetrahydro-2-naphthyl)benzaldehyde

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

700 ml of DME, 2.4 g (2 mmol) of tetrakistriphenylphosphinepalladium(0) and 8.44 g (45.6 mmol) of 3-bromobenzaldehyde are introduced into a three-necked flask under a stream of nitrogen and the mixture is stirred for 10 minutes. A solution of 17 g (69.1 mmol) of 3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydro-2-naphthylboronic acid in 25 ml of ethanol are then added, followed by 46 ml (91 mmol) of potassium carbonate solution (2 M) and the mixture is refluxed for four hours. The reaction medium is cooled and filtered and the solid is washed with bicarbonate solution and then with ethyl acetate. The solid obtained is recrystallized from ethanol and 7 g (50%) of the expected aldehyde are collected, with a melting point of 104-5° C.

Aufarbeitung

  1. temperaturethe mixture is refluxed for four hours
  2. temperatureThe reaction medium is cooled
  3. filtrationfiltered
  4. washthe solid is washed with bicarbonate solution
  5. customThe solid obtained
  6. customis recrystallized from ethanol and 7 g (50%) of the expected aldehyde
  7. customare collected, with a melting point of 104-5° C.

Quellen und Nachweise

ORD-Eintrag
ord-bd3dd6ec556845eb9e19d5ee70fb89a7
Quelldatensatz
uspto-grants-2004_11
Patentnummer
US06825360B1

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