Water → 4-hydroxy-3-[3-[3-(cyanomethoxy)phenyl]-1-oxo-2-propenyl]-2H-1-benzopyran-2-one

HRID 639741

Reaction equation

HRID 639741 reaction equation
[C:1]([C:4]1[C:5](=[O:15])[O:6][C:7]2[CH:14]=[CH:13][CH:12]=[CH:11][C:8]=2[C:9]=1[OH:10])(=[O:3])[CH3:2].[C:16]([CH2:18][O:19][C:20]1[CH:21]=[C:22]([CH:25]=[CH:26][CH:27]=1)[CH:23]=O)#[N:17].N1CCCCC1.O>C(Cl)(Cl)Cl>[OH:10][C:9]1[C:8]2[CH:11]=[CH:12][CH:13]=[CH:14][C:7]=2[O:6][C:5](=[O:15])[C:4]=1[C:1](=[O:3])[CH:2]=[CH:23][C:22]1[CH:25]=[CH:26][CH:27]=[C:20]([O:19][CH2:18][C:16]#[N:17])[CH:21]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8082PiperidineHCID 47669982-(3-Formylphenoxy)acetonitrileHCID 546774033-Acetyl-4-hydroxy-2H-chromen-2-one

Product 1

HCID 761840254-hydroxy-3-[3-[3-(cyanomethoxy)phenyl]-1-oxo-2-propenyl]-2H-1-benzopyran-2-oneYield 57.8%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

In 5 ml of chloroform were dissolved 0.57 g of 3-acetyl-4-hydroxy-2H-1-benzopyran-2-one, 0.45 g of 3-(cyanomethoxy)benzaldehyde and 0.20 g of piperidine, and the solution was heated under refluxing for 1 hour and 30 minutes while water was removed with a Soxhlet's extractor filled with a molecular sieve. After cooling to room temperature, the reaction mixture washed successively with 10% hydrochloric acid and an aqueous saturated sodium chloride solution, dried over anhydrous magnesium sulfate, and concentrated. Precipitated crystals were washed with a mixture of 10 ml of dioxane and 10 ml of chloroform, and washed with 10 ml of t-butyl methyl ether to obtain 0.56 g of 4-hydroxy-3-[3-[3-(cyanomethoxy)phenyl]-1-oxo-2-propenyl]-2H-1-benzopyran-2-one [Compound No. (14d)] as a yellow crystal.

Workup

  1. temperaturethe solution was heated
  2. customwas removed with a Soxhlet's extractor
  3. additionfilled with a molecular sieve
  4. washthe reaction mixture washed successively with 10% hydrochloric acid
  5. dry with materialan aqueous saturated sodium chloride solution, dried over anhydrous magnesium sulfate
  6. concentrationconcentrated
  7. customPrecipitated crystals
  8. washwere washed with a mixture of 10 ml of dioxane and 10 ml of chloroform
  9. washwashed with 10 ml of t-butyl methyl ether

Sources & evidence

ORD record
ord-b8727b415aa34dfa8fb07d4d5e3889ed
Source dataset
uspto-grants-2010_04
Patent number
US07691883B2

Linked notes

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