Furfural → HCID 20366325, compound

HRID 616853Notes

Reaction equation

HRID 616853 reaction equation
[Mg].BrBr.Br[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][C:11]1[O:12][CH:13]([CH3:19])[CH2:14][C:15]([CH3:18])([CH3:17])[N:16]=1.[CH:20](=[O:26])[C:21]1[O:25][CH:24]=[CH:23][CH:22]=1.[Cl-].[NH4+]>CCOCC.O>[O:25]1[CH:24]=[CH:23][CH:22]=[C:21]1[CH:20]([OH:26])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][C:11]1[O:12][CH:13]([CH3:19])[CH2:14][C:15]([CH3:18])([CH3:17])[N:16]=1

Participants

8

Reactant 5

HCID 7362FurfuralHCID 24408BromineHCID 25517Ammonium ChlorideHCID 5462224MagnesiumHCID 203663232-(6-Bromohexyl)-4,4,6-trimethyl-5,6-dihydro-4H-1,3-oxazine

Product 1

HCID 20366325HCID 20366325, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent3×

Procedure

To a stirred suspension of 0.61g (25 mg. atom) of magnesium in 30 ml of ether is added 1.76g (11 mmol) of bromine dropwise during 20 min. at 15°-20° C. After 15 min. the mixture is treated dropwise with a solution of 2.90g (10 mmol) of 2-(6-bromohexyl)-4,4,6-trimethyl-5,6-dihydro-1,3-oxazine [J. Org. Chem., 38, 36(1973)] in 5 ml of ether. The resulting mixture is stirred at ambient temperature for 3 hr. and at reflux temperature for 30 min. The mixture is cooled to 0° and treated during 20 min. with a solution of 1.15g (12 mmol) of furfural. The stirred mixture is brought to reflux temperature during 20 min., maintained at that temperature for 20 min., cooled and treated with 2.5 ml of saturated ammonium chloride. The mixture is diluted with ether and water and filtered. The organic phase is separated, washed with brine, dried over potassium carbonate, and concentrated.

Workup

  1. temperatureand at reflux temperature for 30 min
  2. temperatureThe mixture is cooled to 0°
  3. temperatureto reflux temperature during 20 min.
  4. temperaturemaintained at that temperature for 20 min.
  5. temperaturecooled
  6. filtrationfiltered
  7. customThe organic phase is separated
  8. washwashed with brine
  9. dry with materialdried over potassium carbonate
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-8386d62941c84a42b42d1eb50fee4a13
Source dataset
uspto-grants-1978_02
Patent number
US04076732

Reaction notes

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