Acetonitrile → HCID 20310686, compound

HRID 1763715Notes

Reaction equation

HRID 1763715 reaction equation
[O:1]=[C:2]1[C:8]2[CH:9]=[CH:10][C:11]([CH:13]([CH3:17])[C:14](Cl)=[O:15])=[CH:12][C:7]=2[CH:6]=[CH:5][C:4]2[CH:18]=[CH:19][CH:20]=[CH:21][C:3]1=2.C(#N)C.[CH2:25]([OH:28])[CH:26]=[CH2:27]>C(N(CC)CC)C>[O:1]=[C:2]1[C:8]2[CH:9]=[CH:10][C:11]([CH:13]([CH3:17])[C:14]([O:28][CH2:25][CH:26]=[CH2:27])=[O:15])=[CH:12][C:7]=2[CH:6]=[CH:5][C:4]2[CH:18]=[CH:19][CH:20]=[CH:21][C:3]1=2

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 7858Allyl AlcoholHCID 203106912-(5-oxo-5H-dibenzo[a,d]cyclohepten-2-yl)propionyl chloride

Product 1

HCID 20310686HCID 20310686, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

0.5 G. of 2-(5-oxo-5H-dibenzo[a,d]cyclohepten-2-yl)propionyl chloride is dissolved in 25 ml. of acetonitrile containing 0.5 ml. of allyl alcohol and 0.5 ml. of triethylamine. After 16 hours the mixture is evaporated to dryness and partitioned between ethyl acetate and water. The organic solution is washed, dried, passed through a short (10 g.) silica gel column, then evaporated to give allyl 2-(5-oxo-5H-dibenzo[a,d]cyclohepten-2-yl)propionate as an oil [nmr spectrum in deuterochloroform relative to tetramethylsilane: 1.54 (doublet, CH3), 2.84 (quartet, CH), 4.55 (doublet, OCH2), 5.1-6.0 (multiplet, CH=CH2) and 7.00 ppm (singlet, 10, 11-H); mass spectrum: 318(M+) 233,205].

Workup

  1. customAfter 16 hours the mixture is evaporated to dryness
  2. custompartitioned between ethyl acetate and water
  3. washThe organic solution is washed
  4. customdried
  5. customevaporated

Sources & evidence

ORD record
ord-955acc56c1ef435a93e7cdb6cac649ce
Source dataset
uspto-grants-1978_09
Patent number
US04112114

Reaction notes

Loading…