Ammonium Chloride → 10-(2-dimethylaminoethyl)-10,11-dihydro-5-trimethylsilylmethyl-5H-dibenzo[a,d]cyclohepten-5-ol

HRID 1731200Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1731200
[CH3:1][Si:2]([CH2:5]Cl)([CH3:4])[CH3:3].[Mg].[CH3:8][N:9]([CH3:28])[CH2:10][CH2:11][CH:12]1[C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=2[C:16](=[O:23])[C:15]2[CH:24]=[CH:25][CH:26]=[CH:27][C:14]=2[CH2:13]1.[Cl-].[NH4+]>CCOCC>[CH3:28][N:9]([CH3:8])[CH2:10][CH2:11][CH:12]1[C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=2[C:16]([CH2:5][Si:2]([CH3:3])([CH3:4])[CH3:1])([OH:23])[C:15]2[CH:24]=[CH:25][CH:26]=[CH:27][C:14]=2[CH2:13]1

Komponenten

6

Edukt 4

HCID 25517Ammonium ChlorideHCID 75361Silane, (chloromethyl)trimethyl-HCID 5462224MagnesiumHCID 2035929910-(2-dimethylaminoethyl)-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-one

Produkt 1

HCID 2035930310-(2-dimethylaminoethyl)-10,11-dihydro-5-trimethylsilylmethyl-5H-dibenzo[a,d]cyclohepten-5-ol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel2×

Versuchsvorschrift

A Grignard reagent is prepared by conventional techniques from 12.2 g. (0.1 mole) trimethylsilylmethyl chloride and 24.3 g. magnesium metal (0.1 atom) and 200 ml. ether. The resulting solution is treated with 27.9 g. (0.1 mole) of 10-(2-dimethylaminoethyl)-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-one in 100 ml. ether. Stirring is initiated and the mixture is heated at reflux for 5 hours, then cooled in ice and hydrolyzed with 150 ml. of saturated ammonium chloride. The layers are separated and the ether dried over anhydrous magnesium sulfate and evaporated to give 10-(2-dimethylaminoethyl)-10,11-dihydro-5-trimethylsilylmethyl-5H-dibenzo[a,d]cyclohepten-5-ol.

Aufarbeitung

  1. additionThe resulting solution is treated with 27.9 g
  2. temperaturethe mixture is heated
  3. temperatureat reflux for 5 hours
  4. temperaturecooled in ice and hydrolyzed with 150 ml
  5. customThe layers are separated
  6. dry with materialthe ether dried over anhydrous magnesium sulfate
  7. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-584dba3c22e04c119e4692954161535c
Quelldatensatz
uspto-grants-1976_11
Patentnummer
US03994961

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