Water → 2,2-Diethyl-2h-chromene-6-carbonitrile

HRID 704779Notes

Reaction equation

HRID 704779 reaction equation
[CH2:1]([C:3]1([CH2:16][CH3:17])[CH2:8][CH:7](O)[C:6]2[CH:10]=[C:11]([C:14]#[N:15])[CH:12]=[CH:13][C:5]=2[O:4]1)[CH3:2].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.O>C1(C)C=CC=CC=1.C(OCC)(=O)C>[CH2:16]([C:3]1([CH2:1][CH3:2])[CH:8]=[CH:7][C:6]2[CH:10]=[C:11]([C:14]#[N:15])[CH:12]=[CH:13][C:5]=2[O:4]1)[CH3:17]

Participants

6

Reactant 3

HCID 962WaterHCID 521998p-Toluenesulfonic acid monohydrateHCID 147211782,2-diethyl-3,4-dihydro-4-hydroxy-2H-1-benzopyran-6-carbonitrile

Product 1

HCID 147211802,2-Diethyl-2h-chromene-6-carbonitrileYield 69.9%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 2,2-diethyl-3,4-dihydro-4-hydroxy-2H-1-benzopyran-6-carbonitrile (2.28 g) and p-toluenesulfonic acid hydrate (0.19 g) in toluene was refluxed for an hour and 20 minutes with azeotropic removal of the formed water. The reaction mixture was diluted with ethyl acetate, and then washed with water 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 (1:5) as an eluent to give 2,2-diethyl-2H-1-benzopyran-6-carbonitrile (1.47 g).

Workup

  1. washwashed with water and brine successively
  2. dry with materialThe extract was dried over anhydrous magnesium sulfate
  3. customevaporated in vacuo
  4. customThe residue was purified with silica gel column chromatography
  5. additiona mixture of methylene chloride and n-hexane (1:5) as an eluent

Sources & evidence

ORD record
ord-d8b820dac20040b2a06a181bed3416d5
Source dataset
uspto-grants-1991_01
Patent number
US04988723

Reaction notes

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