Diethyl Ether → 3,4-Dihydro-2H-1-benzopyran-2-acetonitrile

HRID 1196030Notes

Reaction equation

HRID 1196030 reaction equation
[C-:1]#[N:2].[Na+].C1(C)C=CC(S(O[CH2:14][CH:15]2[CH2:24][CH2:23][C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[O:16]2)(=O)=O)=CC=1.C(OCC)C>CN(C)C=O>[C:1]([CH2:14][CH:15]1[CH2:24][CH2:23][C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[O:16]1)#[N:2]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 8929Sodium CyanideHCID 9858183HCID 9858183, compound

Product 1

HCID 148384413,4-Dihydro-2H-1-benzopyran-2-acetonitrileYield 58.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

10.6 g (0.216 mol) of sodium cyanide are added to a solution of 57.31 g (0.18 mol) of 2-(p-toluenesulphonyloxymethyl)chroman in 800 ml of absolute dimethylformamide and the whole is heated, while stirring, to 60°. After 10 hours, ice-water is added to the reaction mixture and extraction is carried out with diethyl ether. The combined ethereal phases are washed thoroughly with water, dried over sodium sulphate and concentrated by evaporation in vacuo. 30.0 g (96.2%) of crude product are obtained and are chromatographed on 1000 g of silica gel (0.040-0.063 mm) using toluene as the eluant. 18.16 g (58.2%) of 2-cyanomethylchroman are thus obtained in the form of a yellow oil.

Workup

  1. temperaturethe whole is heated
  2. washThe combined ethereal phases are washed thoroughly with water
  3. dry with materialdried over sodium sulphate
  4. concentrationconcentrated by evaporation in vacuo
  5. custom30.0 g (96.2%) of crude product are obtained
  6. customare chromatographed on 1000 g of silica gel (0.040-0.063 mm)

Sources & evidence

ORD record
ord-3ea909180fe34d018a1a82128d6389f7
Source dataset
uspto-grants-1992_05
Patent number
US05112855

Reaction notes

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