Acetonitrile → 2-(5-oxo-5H-dibenzo[a,d]cyclohepten-2-yl)prop-1-yl acetate

HRID 259508Notes

Reaction equation

HRID 259508 reaction equation
[O:1]=[C:2]1[C:8]2[CH:9]=[CH:10][C:11]([CH:13]([CH3:16])[CH2:14][OH:15])=[CH:12][C:7]=2[CH:6]=[CH:5][C:4]2[CH:17]=[CH:18][CH:19]=[CH:20][C:3]1=2.C(#N)C.[C:24](Cl)(=[O:26])[CH3:25].C(N(CC)CC)C>O>[C:24]([O:15][CH2:14][CH:13]([C:11]1[CH:10]=[CH:9][C:8]2[C:2](=[O:1])[C:3]3[CH:20]=[CH:19][CH:18]=[CH:17][C:4]=3[CH:5]=[CH:6][C:7]=2[CH:12]=1)[CH3:16])(=[O:26])[CH3:25]

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 214093932-(5-oxo-5H-dibenzo[a,d]cyclohepten-2-yl)propan-1-ol

Product 1

HCID 214217822-(5-oxo-5H-dibenzo[a,d]cyclohepten-2-yl)prop-1-yl acetate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

0.5 G. of 2-(5-oxo-5H-dibenzo[a,d]cyclohepten-2-yl)propan-1-ol is dissolved in 15 ml. of acetonitrile and 2 ml. of acetyl chloride and 1.3 ml. of triethylamine are added to the solution. After 1 hour, the mixture is poured into water and extracted with ethyl acetate. The extract is dried and evaporated, then dissolved in ether and passed through a silica gel column, and the eluate evaporated to afford 2-(5-oxo-5H-dibenzo[a,d]cyclohepten-2-yl)prop-1-yl acetate [an oil, nmr spectrum in deuterochloroform relative to tetramethylsilane, 1.33 (doublet, CH3), 1.98 (singlet, acetoxy), 4.23 (doublet, CH2) and 7.02 ppm (singlet, 10H, 11H); mass spectrum: 306 (M+), 246, 234].

Workup

  1. extractionextracted with ethyl acetate
  2. customThe extract is dried
  3. customevaporated
  4. dissolutiondissolved in ether
  5. customthe eluate evaporated

Sources & evidence

ORD record
ord-cf6584b1405947b7a5ff7aba8738307e
Source dataset
uspto-grants-1977_07
Patent number
US04038299

Reaction notes

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