Ethylene Oxide → 10,11-dihydro-5H-dibenzo[a,d]cycloheptene-5-ethanol

HRID 1981195Notes

Reaction equation

HRID 1981195 reaction equation
[CH2:1]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH2:9][C:8]2[C:3](=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH2:2]1.C([Li])CCC.[CH2:21]1[O:23][CH2:22]1>O1CCCC1.CCCCCC>[CH:4]1[C:3]2[CH2:2][CH2:1][C:15]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[CH:9]([CH2:21][CH2:22][OH:23])[C:8]=2[CH:7]=[CH:6][CH:5]=1

Participants

6

Reactant 3

HCID 6354Ethylene OxideHCID 7002910,11-dihydro-5H-dibenzo(a,d)cyclohepteneHCID 178418339Butyllithium

Product 1

HCID 1852151710,11-dihydro-5H-dibenzo[a,d]cycloheptene-5-ethanol

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

A solution of 58.3 g of dibenzosuberane in 750 ml of tetrahydrofuran, stirred under argon, is cooled to about 10° in an ice-bath and treated dropwise with 190 ml of an about 2M solution of butyl lithium in hexane. The dark red solution is heated to boiling under reflux for 2 hours. Ethylene oxide is conducted for 15 minutes into the solution, cooled to about 10°, subsequently the mixture is stirred at room temperature for 1 hour and finally heated to boiling under reflux for an additional 30 minutes. The cooled mixture is poured into 300 ml of ice-cold 3N hydrochloric acid and extracted twice with 2 l of ether each time. The organic extracts are washed with 500 ml of 2N potassium bicarbonate solution, combined, dried over magnesium sulfate and evaporated. The residue is boiled up three times with 50 ml of pentane each time. There is obtained 10,11-dihydro-5H-dibenzo[a,d]cycloheptene-5-ethanol in the form of a very viscous, yellowish oil, Rf: 0.25 (toluene/ethyl acetate, 9:1).

Workup

  1. temperatureis cooled to about 10° in an ice-bath
  2. temperatureThe dark red solution is heated
  3. temperatureunder reflux for 2 hours
  4. temperaturecooled to about 10°
  5. temperaturefinally heated
  6. temperatureunder reflux for an additional 30 minutes
  7. extractionextracted twice with 2 l of ether each time
  8. washThe organic extracts are washed with 500 ml of 2N potassium bicarbonate solution
  9. dry with materialdried over magnesium sulfate
  10. customevaporated

Sources & evidence

ORD record
ord-22a42d5a72814c90b511eb181be9970b
Source dataset
uspto-grants-1985_04
Patent number
US04513002

Reaction notes

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