Ethyl ketone → 2,2-diethyl-3,4-dihydro-4-oxo-2H-1-benzopyran-6-carbonitrile

HRID 704777Notes

Reaction equation

HRID 704777 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][C:11]=1[OH:12])[C:7]#[N:8])(=[O:3])[CH3:2].[CH3:13][CH2:14][C:15](=O)[CH2:16][CH3:17].N1CCCC1>C1(C)C=CC=CC=1.C(OCC)(=O)C>[CH2:14]([C:15]1([CH2:16][CH3:17])[CH2:2][C:1](=[O:3])[C:4]2[CH:5]=[C:6]([C:7]#[N:8])[CH:9]=[CH:10][C:11]=2[O:12]1)[CH3:13]

Participants

6

Reactant 3

HCID 7288Ethyl ketoneHCID 31268PyrrolidineHCID 123328323-Acetyl-4-hydroxybenzonitrile

Product 1

HCID 143013512,2-diethyl-3,4-dihydro-4-oxo-2H-1-benzopyran-6-carbonitrile

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of 3-acetyl-4-hydroxybenzonitrile (10.48 g) and 3-pentanone (10.3 ml) in toluene (20 ml) was added pyrrolidine (2.7 ml) at ambient temperature. The reaction mixture was stirred overnight at the same temperature and for 3.5 hours under reflux, diluted with ethyl acetate, and then washed with water, 10% aqueous hydrochloric acid, saturated sodium bicarbonate solution and brine successively. The extract was dried over anhydrous magnesium sulfate and evaporated in vacuo. The residue was purified with silica gel column chromatography using a mixture of methylene chloride and n-hexane (1:10→1:1) as an eluent. The fractions containing the object compound were concentrated in vacuo and the residue was triturated to give 2,2-diethyl-3,4-dihydro-4-oxo-2H-1-benzopyran-6-carbonitrile (2.51 g).

Workup

  1. temperatureunder reflux
  2. washwashed with water, 10% aqueous hydrochloric acid, saturated sodium bicarbonate solution and brine successively
  3. dry with materialThe extract was dried over anhydrous magnesium sulfate
  4. customevaporated in vacuo
  5. customThe residue was purified with silica gel column chromatography
  6. additiona mixture of methylene chloride and n-hexane (1:10→1:1) as an eluent
  7. additionThe fractions containing the object compound
  8. concentrationwere concentrated in vacuo
  9. customthe residue was triturated

Sources & evidence

ORD record
ord-a1a9a1c8b54049eda0fef6fe863fb75e
Source dataset
uspto-grants-1991_01
Patent number
US04988723

Reaction notes

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