Allyl Alcohol → HCID 22645452, compound

HRID 2414374Notes

Reaction equation

HRID 2414374 reaction equation
[CH3:1][C:2]1[O:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.[Br:9]N1C(=O)CCC1=O.[CH2:17]([OH:20])[CH:18]=[CH2:19]>C(Cl)(Cl)(Cl)Cl>[Br:9][CH2:1][C:2]1[O:8][C:5]([C:6]([O:20][CH2:17][CH:18]=[CH2:19])=[O:7])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 7858Allyl AlcoholHCID 120975-MethylfurfuralHCID 67184N-bromobutanimide

Product 1

HCID 22645452HCID 22645452, compound

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To a solution of 5-methylfurfural (18 mL, 0.18 mmol) in CCl4 (400 mL) is added pulverized N-bromosuccinimide (71.1 g, 0.40 mmol), and the solution is subjected to sun lamp irradiation. After 15 minutes, the solution begins to reflux vigorously, and then settles down after another 2-3 minutes. After an additional 10 minutes, the dark mixture is cooled to room temperature, and allyl alcohol (200 mL) is added. After 2 hours, the solution is evaporated, and the residue is diluted with Et2O, and washed with saturated NaHCO3 (100 mL), water (100 mL) and brine (100 mL), dried over MgSO4 and evaporated. The residue is chromatographed (silica, 4% EtOAc/hexane) to yield allyl 5-(bromomethyl)-2-furoate, as a yellow oil.

Workup

  1. customthe solution is subjected to sun lamp
  2. customirradiation
  3. temperatureto reflux vigorously
  4. waitsettles down after another 2-3 minutes
  5. waitAfter an additional 10 minutes
  6. waitAfter 2 hours
  7. customthe solution is evaporated
  8. additionthe residue is diluted with Et2O
  9. washwashed with saturated NaHCO3 (100 mL), water (100 mL) and brine (100 mL)
  10. dry with materialdried over MgSO4
  11. customevaporated
  12. customThe residue is chromatographed (silica, 4% EtOAc/hexane)

Sources & evidence

ORD record
ord-4548842765664c36a34ecdb7625f6448
Source dataset
uspto-grants-2004_11
Patent number
US06812237B2

Reaction notes

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