Diethyl Ether → HCID 54515481, compound

HRID 1822806Notes

Reaction equation

HRID 1822806 reaction equation
C[O-].[Na+].[O:4]1[CH:8]=[CH:7][C:6]([CH:9]=O)=[CH:5]1.[N+:11]([CH3:14])([O-:13])=[O:12].CCOCC>CO>[N+:11]([CH:14]=[CH:9][C:6]1[CH:7]=[CH:8][O:4][CH:5]=1)([O-:13])=[O:12]

Participants

6

Conditions

Temperature
0 °C

Procedure

A freshly prepared solution of sodium methoxide (prepared by dissolving sodium (0.46 g, 20 mmol) in MeOH (5 mL)) was added very slowly via a double ended needle to a solution of 3-furaldehyde (1.73 mL, 20 mM) and nitromethane (1.08 mL, 20 mmol) in MeOH (4 mL) cooled to 0° C. The mixture was stirred at 0° C. an addition 5 min, then Et2O (10 mL) was added. The resultant salt was collected via filtration, thoroughly washed with Et2O, taken up in a minimum amount of water then the solution was added to an ice cold solution of 25% HCl (80 mL). The solid that formed was collected by filtration and washed with water, then the moist product was taken up in CHCl3/MeOH and solvents removed to give 3-(2-nitrovinyl) furan (69%) as a pale yellow solid.

Workup

  1. additionan addition 5 min
  2. filtrationThe resultant salt was collected via filtration
  3. washthoroughly washed with Et2O
  4. additionthe solution was added to an ice cold solution of 25% HCl (80 mL)
  5. customThe solid that formed
  6. filtrationwas collected by filtration
  7. washwashed with water
  8. customsolvents removed

Sources & evidence

ORD record
ord-c5aa1c8f67fa4aba9972532c3f5d28ce
Source dataset
uspto-grants-2006_05
Patent number
US07037916B2

Reaction notes

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