Nitromethane → HCID 11355984, compound

HRID 2213328Notes

Reaction equation

HRID 2213328 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[CH:6]=[O:7])#[N:2].[N+:11]([CH3:14])([O-:13])=[O:12].C(NCC)C>C1COCC1>[OH:7][CH:6]([C:5]1[CH:4]=[C:3]([CH:10]=[CH:9][CH:8]=1)[C:1]#[N:2])[CH2:14][N+:11]([O-:13])=[O:12]

Participants

5

Reactant 3

HCID 6375NitromethaneHCID 8021DiethylamineHCID 90670m-Formylbenzonitrile

Product 1

HCID 11355984HCID 11355984, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-Cyanobenzaldehyde (3.0 g, 22.9 mmol), nitromethane (4.2 g, 68.7 mmol) and diethylamine (167 mg, 2.29 mmol) were stirred for 48 h in THF at 55° C. in the presence of 4 Å molecular sieves. The resulting reaction mixture was filtered through celite and the resulting solution was concentrated in vacuo, then partitioned between EtOAc (20 mL) and H2O (100 mL). The EtOAc layer was washed with H2O (2×75 mL) and brine (1×50 mL), then dried (MgSO4), filtered, and concentrated in vacuo. The resulting residue was filtered through silica gel, eluting with hexanes:EtOAc (2:1) to obtain 3-(1-hydroxy-2-nitroethyl)benzonitrile as a pale yellow solid.

Workup

  1. customThe resulting reaction mixture
  2. filtrationwas filtered through celite
  3. concentrationthe resulting solution was concentrated in vacuo
  4. custompartitioned between EtOAc (20 mL) and H2O (100 mL)
  5. washThe EtOAc layer was washed with H2O (2×75 mL) and brine (1×50 mL)
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. filtrationThe resulting residue was filtered through silica gel
  10. washeluting with hexanes:EtOAc (2:1)

Sources & evidence

ORD record
ord-bea19e25a1c7405aa0d130569fb2cb3a
Source dataset
uspto-grants-2006_09
Patent number
US07105548B2

Reaction notes

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