Hydrochloric Acid → 2-(2-Nitrovinyl)-5-phenylfuran

HRID 915648

Reaction equation

HRID 915648 reaction equation
[C:1]1([C:7]2[O:11][C:10]([CH:12]=O)=[CH:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CO.[OH-].[Na+].Cl.[N+:19]([CH3:22])([O-:21])=[O:20]>O>[N+:19]([CH:22]=[CH:12][C:10]1[O:11][C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[CH:8][CH:9]=1)([O-:21])=[O:20]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 887MethanolHCID 6375NitromethaneHCID 14798Sodium HydroxideHCID 27694205-Phenyl-2-furaldehyde

Product 1

HCID 8012792-(2-Nitrovinyl)-5-phenylfuran

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

Combine 5-phenylfuran-2-carbaldehyde (808 mg, 4.69 mmol), methanol (2.0 mL), and nitromethane (1.13 mL) and cool. Add a combination of 0.20 mL of 1M sodium hydroxide and 0.70 mL of water to the reaction. Stir the reaction for 15 minutes, dilute with water (5 mL), add 1.0 mL of concentrated hydrochloric acid, and stir for 20 additional hours. Extract the reaction with ethyl acetate, dry organics, filter and evaporate to yield 1.14 g of 2-(2-nitrovinyl)-5-phenylfuran as a brown oil which can be used without further purification. MH+ 216.0

Workup

  1. customto the reaction
  2. customthe reaction for 15 minutes
  3. stirringstir for 20 additional hours
  4. extractionExtract
  5. customthe reaction with ethyl acetate
  6. filtrationdry organics, filter
  7. customevaporate

Sources & evidence

ORD record
ord-3025f83ffd4745d8b39fa8720adb10a3
Source dataset
uspto-grants-2007_09
Patent number
US07265246B2

Linked notes

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