Coumaranone → Benzofuran-3-acetonitrile

HRID 431785

Reaction equation

HRID 431785 reaction equation
[H-].[Na+].CCOP(OCC)([CH2:8][C:9]#[N:10])=O.[O:14]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:16](=O)[CH2:15]1>C1COCC1.CCOC(C)=O.O>[O:14]1[C:22]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[C:16]([CH2:8][C:9]#[N:10])=[CH:15]1

Participants

7

Reactant 3

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

Product 1

HCID 2769401Benzofuran-3-acetonitrileYield 91%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Sodium hydride (268 mg, 6.7 mmol) was slurried in dry THF (10 ml) at 0° C. under nitrogen and diethyl cyanomethyl phosphonate (1.1 ml, 6.7 mmol) added dropwise and the whole stirred for 45 min. 3-Coumaranone (Lancaster) (900 mg, 6.7 mmol) was then added dropwise and the whole stirred at room temperature for 45 min. The reaction was diluted with EtOAc (15 ml) and water (15 ml), and the organic layer was then separated, dried (MgSO4) and evaporated and the residue flash chromatographed using 0-5% EtOAc in pentane to give the title product (940 mg, 91%); 1HNMR (400 MHz, CDCl3) δ: 3.77 (s, 2H), 7.25-7.40 (m, 2H), 7.52 (dd, 1H), 7.58 (dd, 1H), 7.67 (s, 1H); LRMS: M+NH4+, 175. (TS+).

Workup

  1. stirringthe whole stirred at room temperature for 45 min
  2. customthe organic layer was then separated
  3. dry with materialdried (MgSO4)
  4. customevaporated
  5. customthe residue flash chromatographed

Sources & evidence

ORD record
ord-dcf6a7a44a134677af4f3871218f3b28
Source dataset
uspto-grants-2003_12
Patent number
US06660756B2

Linked notes

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