Furfural → HCID 11831804, compound

HRID 413510Notes

Reaction equation

HRID 413510 reaction equation
[Br:1][C:2]1[CH:14]=[CH:13][CH:12]=[CH:11][C:3]=1[CH2:4]P(=O)(OC)OC.[H-].[Na+].[CH:17](=O)[C:18]1[O:22][CH:21]=[CH:20][CH:19]=1>CN(C=O)C.O>[O:22]1[CH:21]=[CH:20][CH:19]=[C:18]1/[CH:17]=[CH:4]/[C:3]1[CH:11]=[CH:12][CH:13]=[CH:14][C:2]=1[Br:1]

Participants

6

Reactant 3

HCID 7362FurfuralHCID 24758Sodium hydrideHCID 13729876HCID 13729876, compound

Product 1

HCID 11831804HCID 11831804, compoundYield 40.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent3×

Procedure

A solution of dimethyl 2-bromobenzylphosphonate (10.35 g) in dry DMF (50 ml) was added dropwise at room temperature to a stirred suspension of sodium hydride (0.979 g) in dry DMF (100 ml) (effervescence). After 20 minutes, a solution of furfural (3.56 g) in dry DMF (50 ml) was added (exotherm) and the resulting mixture was stirred at room temperature for 4 hours, then diluted with water and extracted with ether. The extracts were washed with water, treated with magnesium sulphate and charcoal, filtered, concentrated under reduced pressure, and chromatographed using 40-60° C. petrol as eluant to give E-1-(2-furyl)-2-(2-bromophenyl)-ethylene (3.755 g), a pale yellow liquid (containing about 6% of the corresponding Z-isomer by GC).

Workup

  1. extractionextracted with ether
  2. washThe extracts were washed with water
  3. additiontreated with magnesium sulphate and charcoal
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customchromatographed
  7. customusing 40-60° C.

Sources & evidence

ORD record
ord-f0367473886844aab199346b5c8ecd10
Source dataset
uspto-grants-2003_05
Patent number
US06566547B1

Reaction notes

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