Hydrochloric Acid → Benzofuran-3-acetonitrile

HRID 2308606Notes

Reaction equation

HRID 2308606 reaction equation
[H-].[Na+].C(OP([CH2:11][C:12]#[N:13])(=O)OCC)C.[O:14]1[CH2:18][C:17](=O)[C:16]2[CH:20]=[CH:21][CH:22]=[CH:23][C:15]1=2.Cl>O1CCCC1>[C:12]([CH2:11][C:17]1[C:16]2[CH:20]=[CH:21][CH:22]=[CH:23][C:15]=2[O:14][CH:18]=1)#[N:13]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 23556CoumaranoneHCID 24758Sodium hydrideHCID 75676Diethyl (cyanomethyl)phosphonate

Product 1

HCID 2769401Benzofuran-3-acetonitrileYield 98%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
70 °C

Procedure

To a suspension of 2.64 gms (0.11 mole) of oil free sodium hydride in 200 ml of tetrahydrofuran (THF) was added dropwise a solution of 19.47 gms (0.11 mole) of diethylcyanomethylphosphonate in 75 mL of THF. After the H2 evolution had ceased, a solution of 13.4 g (0.1 mole) of 3-(2H)-benzo[b]furanone in 100 mL of THF was added. The solution was heated at 70° C. for 1.5 hours, cooled, and poured into 500 mL of 5% HCl, and washed with ether. The ether phase was washed with brine, dried (MgSO4), filtered and concentrated to give 15.4 g of a dark oil. The product was distilled at 96°-100° C./0.075 mm Hg to give 10.85 g of a yellow oil which crystallized upon standing.

Workup

  1. temperaturecooled
  2. washwashed with ether
  3. washThe ether phase was washed with brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-c62368ca22f74eafb9caa5e709040233
Source dataset
uspto-grants-1987_09
Patent number
US04690928

Reaction notes

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