Water → HCID 54545379, compound

HRID 2298878Notes

Reaction equation

HRID 2298878 reaction equation
[H-].[Na+].[C:3]([CH2:5]P(=O)(OCC)OCC)#[N:4].[CH3:14][C:15]1[CH:16]=[CH:17][C:18]2[O:22][CH2:21][C:20](=O)[C:19]=2[CH:24]=1.O>C1COCC1>[CH3:14][C:15]1[CH:16]=[CH:17][C:18]2[O:22][C:21]([CH2:5][C:3]#[N:4])=[CH:20][C:19]=2[CH:24]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 75676Diethyl (cyanomethyl)phosphonateHCID 5905355-Methyl-1-benzofuran-3(2H)-one

Product 1

HCID 54545379HCID 54545379, compoundYield 82.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Reaction under N2 atmosphere. NaH 60% (0.17 mol) was stirred in TBF (350 ml). A solution of diethyl (cyanomethyl)phosphonate (0.17 mol) in THF (150 ml) was added dropwise over ±20 minutes. (exothermic temperature rise to 30° C.). The mixture was stirred for 20 minutes at RT, then cooled to 0° C. A solution of 5-methyl-3-benzo-furanone (0.15 mol) in THF (350 ml) was added dropwise over 30 minutes at 0° C. reaction mixture was stirred overnight at RT, then poured out into water (1500 ml) and stirred. This mixture was extracted with ether, DIPE (2×), dried (MgSO4), filtered and the solvent was evaporated. The residue was purified by column chromatography over silica gel (eluent: CH2Cl2/hexane 50/50). The desired fractions were collected and the solvent was evaporated, yielding 21.2 g (82%) of 5-methyl-3-benzofuranacetonitrile (interm. 3).

Workup

  1. customReaction under N2 atmosphere
  2. custom(exothermic temperature rise to 30° C.)
  3. temperaturecooled to 0° C
  4. customreaction mixture
  5. stirringwas stirred overnight at RT
  6. stirringstirred
  7. extractionThis mixture was extracted with ether, DIPE (2×)
  8. dry with materialdried (MgSO4)
  9. filtrationfiltered
  10. customthe solvent was evaporated
  11. customThe residue was purified by column chromatography over silica gel (eluent: CH2Cl2/hexane 50/50)
  12. customThe desired fractions were collected
  13. customthe solvent was evaporated

Sources & evidence

ORD record
ord-8c88f3a2fc3c4854829e1fa47b6c29d0
Source dataset
uspto-grants-2002_12
Patent number
US06495555B1

Reaction notes

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