Propanenitrile, 3-ethoxy- → 3-(7,8-Dimethoxy-2H-1-benzopyran-5-yl)-2-methoxymethylpropenenitrile

HRID 34466

Reaction equation

HRID 34466 reaction equation
C[O-].[Na+].[CH3:4][O:5][C:6]1[CH:15]=[C:14]([CH:16]=O)[C:9]2[CH:10]=[CH:11][CH2:12][O:13][C:8]=2[C:7]=1[O:18][CH3:19].[CH2:20]([O:22][CH2:23][CH2:24][C:25]#[N:26])C>CO.O.C(OCC)C>[CH3:4][O:5][C:6]1[CH:15]=[C:14]([CH:16]=[C:24]([CH2:23][O:22][CH3:20])[C:25]#[N:26])[C:9]2[CH:10]=[CH:11][CH2:12][O:13][C:8]=2[C:7]=1[O:18][CH3:19]

Participants

7

Reactant 3

HCID 16501Propanenitrile, 3-ethoxy-HCID 10942334Sodium MethoxideHCID 128498327,8-Dimethoxy-5-formyl-2H-1-benzopyran

Product 1

HCID 543734473-(7,8-Dimethoxy-2H-1-benzopyran-5-yl)-2-methoxymethylpropenenitrileYield 73.6%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

A mixture of sodium methoxide (7.02 g, 0.13 mole), 7,8-dimethoxy-5-formyl-2H-1-benzopyran (57 g, 0.26 mole) and 3-ethoxypropanenitrile (28.35 g, 0.286 mole) in methanol (150 mL) was heated at reflux for 4 hr, allowed to cool and diluted with water (150 mL) and ethylether (500 mL). The layers were separated and the ether portion was washed with water (3×250 mL and 1×100 mL) and dried over magnesium sulfate. The ether solution was concentrated to give 55 g (73%) of an amber oil which was used without further purification.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 4 hr
  3. temperatureto cool
  4. customThe layers were separated
  5. washthe ether portion was washed with water (3×250 mL and 1×100 mL)
  6. dry with materialdried over magnesium sulfate
  7. concentrationThe ether solution was concentrated

Sources & evidence

ORD record
ord-5e01e92fc0084880a6a5e07a5002bbca
Source dataset
uspto-grants-1988_08
Patent number
US04761475

Linked notes

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