5H-Dibenzo[a,d]cyclohepten-5-one → HCID 15818605, compound

HRID 1720867Notes

Reaction equation

HRID 1720867 reaction equation
[CH2:1]([Mg]Br)[CH3:2].[CH:5]1[CH:10]=[C:9]2[CH:11]=[CH:12][C:13]3[C:18]([C:19](=[O:20])[C:8]2=[CH:7][CH:6]=1)=[CH:17][CH:16]=[CH:15][CH:14]=3.[Cl-].[NH4+]>CCOCC>[CH2:8]([C:19]1([OH:20])[C:18]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[CH:12]=[CH:11][C:9]2[CH:10]=[CH:5][CH:6]=[CH:1][C:2]1=2)[CH3:7]

Participants

5

Reactant 3

HCID 166795H-Dibenzo[a,d]cyclohepten-5-oneHCID 25517Ammonium ChlorideHCID 178418443HCID 178418443, compound

Product 1

HCID 15818605HCID 15818605, compoundYield 93.8%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To 150 mmol of ethyl magnesium bromide in 150 ml of ether are added 10 g (48.5 mmol) of dibenzosuberenone in 250 ml of ether at 0° C. After 3 hours at about 10° C., the mixture is cooled in an ice bath and 40 ml of saturated aqueous ammonium chloride are added slowly. Extractions of the aqueous phase with ether affords 10.75 g of a yellow oily residue. Purification by flash chromatography yields 8.5 g (74%) of the expected product.

Workup

  1. temperaturethe mixture is cooled in an ice bath
  2. extractionExtractions of the aqueous phase with ether

Sources & evidence

ORD record
ord-d006935632f849e2bf6f4ff1754f110e
Source dataset
uspto-grants-1996_04
Patent number
US05508280

Reaction notes

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