Acetic Acid → HCID 10679379, compound

HRID 1087021Notes

Reaction equation

HRID 1087021 reaction equation
[O:1]1[CH2:6][CH2:5][C:4](=O)[CH2:3][CH2:2]1.[C:8]([CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])#[N:9].C([O-])(=O)C.[NH4+].C(O)(=O)C>C1(C)C=CC=CC=1>[CH2:14]([O:13][C:11]([C:10]([C:8]#[N:9])=[C:4]1[CH2:5][CH2:6][O:1][CH2:2][CH2:3]1)=[O:12])[CH3:15]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 7764Ethyl cyanoacetateHCID 121599Tetrahydro-4H-pyran-4-oneHCID 517165Ammonium Acetate

Product 1

HCID 10679379HCID 10679379, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

A mixture of tetrahydropyran-4-one (12 g), ethyl cyanoacetate (13.6 g), ammonium acetate (1.2 g), glacial acetic acid (2.4 ml) and toluene (15 ml) is stirred at reflux for 16 hours. The mixture is diluted with toluene and the organic layer is separated, washed with water, then brine, and dried over magnesium sulfate. It is concentrated at reduced pressure to an oil which solidifies. It is further purified by flash chromatography through silica gel with methylene chloride as eluent. The desired fractions are combined and concentrated to dryness at reduced pressure to afford 4-(alpha-ethoxycarbonyl-cyanomethylene)-tetrahydropyran.

Workup

  1. temperatureat reflux for 16 hours
  2. customthe organic layer is separated
  3. washwashed with water
  4. dry with materialbrine, and dried over magnesium sulfate
  5. concentrationIt is concentrated at reduced pressure to an oil which
  6. customIt is further purified by flash chromatography through silica gel with methylene chloride as eluent
  7. concentrationconcentrated to dryness at reduced pressure

Sources & evidence

ORD record
ord-6479001f778e4d92849c58b9dfc4ba4b
Source dataset
uspto-grants-1991_07
Patent number
US05034381

Reaction notes

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