Water → HCID 54104378, compound

HRID 582609Notes

Reaction equation

HRID 582609 reaction equation
C1(C)C=CC(S(O[CH2:11][CH2:12][CH:13]2[CH2:18][CH2:17][C:16]3[CH:19]=[CH:20][CH:21]=[CH:22][C:15]=3[O:14]2)(=O)=O)=CC=1.[C-:24]#[N:25].[K+].O>CS(C)=O>[C:24]([CH2:11][CH2:12][CH:13]1[CH2:18][CH2:17][C:16]2[CH:19]=[CH:20][CH:21]=[CH:22][C:15]=2[O:14]1)#[N:25]

Participants

5

Reactant 3

HCID 962WaterHCID 9032Potassium CyanideHCID 14838443HCID 14838443, compound

Product 1

HCID 54104378HCID 54104378, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture of 15.8 g (47 mmol) of 2-p-toluenesulfonyloxyethyl-3,4-dihydro-2H-1-benzopyran and 3.4 g (52 mmol) of potassium cyanide in 320 ml of dimethyl sulfoxide is stirred for 2 hours. After addition of water, the product is extracted with chloroform containing a little methanol and then the organic phase is washed with a saturated solution of sodium chloride, dried over sodium sulfate and concentrated under reduced pressure. By chromatography of the residue on a silica column using cyclohexane containing 10% ethyl acetate, 7.8 g of compound are obtained in oil form.

Workup

  1. extractionthe product is extracted with chloroform containing a little methanol
  2. washthe organic phase is washed with a saturated solution of sodium chloride
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customare obtained in oil form

Sources & evidence

ORD record
ord-778a16fbc04e4a699d3c0ab6f826f838
Source dataset
uspto-grants-1999_07
Patent number
US05925662

Reaction notes

Loading…