Hydrochloric Acid → Benzofuran-3-acetonitrile

HRID 2073348Notes

Reaction equation

HRID 2073348 reaction equation
[H-].[Na+].[C:3]([CH2:5]P(=O)(OCC)OCC)#[N:4].[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:3]([CH2:5][C:17]1[C:16]2[CH:20]=[CH:21][CH:22]=[CH:23][C:15]=2[O:14][CH:18]=1)#[N:4]

Participants

6

Reactant 4

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

Product 1

HCID 2769401Benzofuran-3-acetonitrile

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
70 °C

Procedure

To a suspension of 2.64 grams (0.11 mole) of oil free sodium hydride in 200 milliliters of tetrahydrofuran (THF) was added dropwise a solution of 19.47 grams (0.11 mole) of diethyl cyanomethylphosphonate in 75 milliliters of THF. After the H2 evolution had ceased, a solution of 13.4 grams (0.1 mole) of 3-(2H)-benzo[b]furanone in 100 milliliters of THF was added. The solution was heated at 70° C. for 1.5 hours, cooled, and poured into 500 milliliters of 5% HCl, and worked up using conventional procedures and finally distilled at 96°-100° C./0.075 mm Hg to obtain a yellow oil product which crystallized upon standing.

Workup

  1. temperaturecooled
  2. distillationfinally distilled at 96°-100° C./0.075 mm Hg
  3. customto obtain a yellow oil product which
  4. customcrystallized

Sources & evidence

ORD record
ord-c4ccc8cdf16a448e8c49bef1e1e8a250
Source dataset
uspto-grants-1990_04
Patent number
US04916223

Reaction notes

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