Sodium Iodide → 1-(2-Cyanoethyl)isochroman

HRID 1417798Notes

Reaction equation

HRID 1417798 reaction equation
Cl[CH2:2][CH2:3][CH:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:7][CH2:6][O:5]1.[C-]#N.[Na+].[I-].[Na+].[CH3:19][N:20](C=O)C>O>[C:19]([CH2:2][CH2:3][CH:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:7][CH2:6][O:5]1)#[N:20]

Participants

6

Reactant 4

HCID 5238Sodium Iodide2×HCID 6228Dimethylformamide2×HCID 8929Sodium Cyanide2×HCID 106079661-(2-Chloroethyl)isochroman

Product 1

HCID 142030711-(2-Cyanoethyl)isochroman

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 1-(2-chloroethyl)isochroman (LXIV, PREPARATION 2, 0.9874 g, 5.02 mmol), sodium cyanide (0.3793 g, 7.74 mmol), sodium iodide (a few mg) and DMF (5 ml) is heated overnight at 856. Additional sodium cyanide (0.5826 g, 11.9 mmol) is then added in two portions, along with DMF (14 ml) and a few mgs of sodium iodide. The mixture is heated at 97° for another two days and then cooled and poured into water. The mixture is extracted several times with ethyl acetate and the combined organic phase is backwashed twice with water, followed by two saline washes, then dried over magnesium sulfate and concentrated to dryness. The crude product is chromatographed on silica gel eluting with ethyl acetate/hexane (10/90). The appropriate fractions are pooled and concentrated to give 1-(2-cyanoethyl)isochroman (LXVI), NMR (CDCl3) 2.11, 2.27-2.72, 2.98, 3.77, 4.13, 4.86 and 7.17 δ.

Workup

  1. temperatureis heated overnight at 856
  2. temperatureThe mixture is heated at 97° for another two days
  3. temperaturecooled
  4. extractionThe mixture is extracted several times with ethyl acetate
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated to dryness
  7. customThe crude product is chromatographed on silica gel eluting with ethyl acetate/hexane (10/90)
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-d7fad628c72a4afbaeb72d3f8a753287
Source dataset
uspto-grants-1999_03
Patent number
US05877317

Reaction notes

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