Iodoethane → 1-ethoxy-2-(5-oxo-5H-dibenzo[a,d]cyclohepten-2-yl)propane

HRID 259509Notes

Reaction equation

HRID 259509 reaction equation
[H-].[Na+].[O:3]=[C:4]1[C:10]2[CH:11]=[CH:12][C:13]([CH:15]([CH3:18])[CH2:16][OH:17])=[CH:14][C:9]=2[CH:8]=[CH:7][C:6]2[CH:19]=[CH:20][CH:21]=[CH:22][C:5]1=2.[H][H].[CH2:25](I)[CH3:26]>CCOCC.O.CN(C)C=O>[CH2:25]([O:17][CH2:16][CH:15]([C:13]1[CH:12]=[CH:11][C:10]2[C:4](=[O:3])[C:5]3[CH:22]=[CH:21][CH:20]=[CH:19][C:6]=3[CH:7]=[CH:8][C:9]=2[CH:14]=1)[CH3:18])[CH3:26]

Participants

8

Reactant 4

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 214093932-(5-oxo-5H-dibenzo[a,d]cyclohepten-2-yl)propan-1-olHCID 178418361HCID 178418361, compound

Product 1

HCID 214217901-ethoxy-2-(5-oxo-5H-dibenzo[a,d]cyclohepten-2-yl)propane

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
40 °C

Procedure

0.48 G. of a 50% mineral oil dispersion of sodium hydride is added to a solution of 2.64 g. of 2-(5-oxo-5H-dibenzo[a,d]cyclohepten-2-yl)propan-1-ol in 30 ml. of dimethylformamide. The mixture is warmed to 40° C. and stirred until hydrogen evolution ceases. 3.0 G. of ethyl iodide is added and the mixture heated to 60° C. for 3 hrs. Water and ether are added and the ethereal solution is washed with water, dried and evaporated to yield 1-ethoxy-2-(5-oxo-5H-dibenzo[a,d]cyclohepten-2-yl)propane.

Workup

  1. temperaturethe mixture heated to 60° C. for 3 hrs
  2. washthe ethereal solution is washed with water
  3. customdried
  4. customevaporated

Sources & evidence

ORD record
ord-5207e6d1b11749668cdb1b2310e805ed
Source dataset
uspto-grants-1977_07
Patent number
US04038299

Reaction notes

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