Pyridine → 2,3-Dihydro-7-benzofuranacetonitrile

HRID 440513Notes

Reaction equation

HRID 440513 reaction equation
C1(C)C=CC=CC=1.[C:8]1(=O)[O:13][C:11](=O)[C:10]2=[CH:14][CH:15]=[CH:16][CH:17]=[C:9]12.[N:19]1C=CC=[CH:21][CH:20]=1>>[O:13]1[CH2:11][CH2:10][C:14]2[CH:15]=[CH:16][CH:17]=[C:9]([CH2:21][C:20]#[N:19])[C:8]1=2

Participants

4

Reactant 3

HCID 1049PyridineHCID 1140TolueneHCID 6811Phthalic Anhydride

Product 1

HCID 224067282,3-Dihydro-7-benzofuranacetonitrile

Procedure

A mixture of the oil, toluene (60 ml), pyridine (2.2 ml) and phthalic anhydride (4 g) was heated at 90°-95° C. for 4 hours. The resulting solution was cooled, washed with 10% aqueous potassium carbonate solution, then with dilute hydrochloric acid. The solution was then dried over sodium sulphate and the solvent removed in vacuo to yield an oil. The oil was distilled, (b.p. 120° C./1 mbar) to give 2,3-dihydrobenzo[b]furan-7-ylacetonitrile which rapidly solidified (16.97 g).

Workup

  1. temperaturewas heated at 90°-95° C. for 4 hours
  2. temperatureThe resulting solution was cooled
  3. washwashed with 10% aqueous potassium carbonate solution
  4. dry with materialThe solution was then dried over sodium sulphate
  5. customthe solvent removed in vacuo
  6. customto yield an oil
  7. distillationThe oil was distilled

Sources & evidence

ORD record
ord-d05875b1d0ee4734ba6d34f3c8ae2a62
Source dataset
uspto-grants-1996_05
Patent number
US05519034

Reaction notes

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