Diethyl Ether → HCID 10889914, compound

HRID 2226742Notes

Reaction equation

HRID 2226742 reaction equation
[CH:1]1[C:11]2[CH2:10][CH2:9][C:8]3[CH:12]=[CH:13][CH:14]=[CH:15][C:7]=3[C:6](=[O:16])[C:5]=2[CH:4]=[CH:3][CH:2]=1.[CH:17]([Mg]Br)=[CH2:18].[Cl-].[NH4+].C(OCC)C>C1COCC1.O>[CH:17]([C:6]1([OH:16])[C:7]2[CH:15]=[CH:14][CH:13]=[CH:12][C:8]=2[CH2:9][CH2:10][C:11]2[CH:1]=[CH:2][CH:3]=[CH:4][C:5]1=2)=[CH2:18]

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 14589DibenzosuberoneHCID 25517Ammonium ChlorideHCID 178418507HCID 178418507, compound

Product 1

HCID 10889914HCID 10889914, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-one (9.4 g, 0.045 mol) in dry THF (100 ml) was placed under an atmosphere of nitrogen. A solution of vinylmagnesium bromide in THF (100 ml, 0.5 M) was added in such a rate to keep the reaction temperature at 30°-35° C. When addition was complete the mixture was heated at 50°-60° C. for 1.5 h. The reaction mixture was cooled on an ice-bath and a solution of ammonium chloride (10 g) in water (50 ml) was carefully added. Diethyl ether (100 ml) was added and the phases were separated. The aqueous phase was extracted with diethyl ether (100 ml) and the combined organic phases were dried over sodium sulphate. The solvent was evaporated in vacuo to give a residue which was re-evaporated twice with dichloromethane to give 11.8 g of crude 5-ethenyl-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ol.

Workup

  1. customat 30°-35° C
  2. additionWhen addition
  3. temperaturewas heated at 50°-60° C. for 1.5 h
  4. temperatureThe reaction mixture was cooled on an ice-bath
  5. customthe phases were separated
  6. extractionThe aqueous phase was extracted with diethyl ether (100 ml)
  7. dry with materialthe combined organic phases were dried over sodium sulphate
  8. customThe solvent was evaporated in vacuo
  9. customto give a residue which
  10. customwas re-evaporated twice with dichloromethane

Sources & evidence

ORD record
ord-613e54c00050452c953a4fe923e1f071
Source dataset
uspto-grants-1994_09
Patent number
US05348965

Reaction notes

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