Benzyl Bromide → HCID 57213189, compound

HRID 1941233Notes

Reaction equation

HRID 1941233 reaction equation
[OH:1][C:2]1[C:11]2[O:10][C:9](=[CH:12][N:13]3[CH2:18][CH2:17][O:16][CH2:15][CH2:14]3)[CH2:8][C:7](=[O:19])[C:6]=2[CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:26](Br)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>C(#N)C>[CH2:26]([O:1][C:2]1[C:11]2[O:10][C:9](=[CH:12][N:13]3[CH2:14][CH2:15][O:16][CH2:17][CH2:18]3)[CH2:8][C:7](=[O:19])[C:6]=2[CH:5]=[CH:4][CH:3]=1)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 57282510HCID 57282510, compound

Product 1

HCID 57213189HCID 57213189, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
70 °C

Procedure

8-Hydroxy-2-(4-morpholinylmethylene)-4H-1-benzopyran-4-one (261 mg, 1 mmole) is suspended in 7 ml acetonitrile in a 25 ml one neck round bottom flask under nitrogen. The suspension is treated successively with potassium carbonate (829 mg, 6 mmole) and benzyl bromide (150ul, 1.3 mmole) and the reaction mixture is warmed to 70° C. for 1 h. The mixture is cooled to room temperature and the acetonitrile is removed in vacuo. The residue is washed with 1×25 ml dichloromethane and the insoluble material is removed by filtration. The filtrate is concentrated in vacuo to a yellow oil. The oil is chromatographed over 15 g silica gel (230-400 mesh)eluting with 3% methanol/dichloromethane and collecting 6 ml fractions. Fractions 12-27 are combined and concentrated to afford a colorless oil which is crystallized from diethyl ether to provide 246 mg (70%) of the title compound as a white solid, mp. 107°-107.5° C.

Workup

  1. temperatureThe mixture is cooled to room temperature
  2. customthe acetonitrile is removed in vacuo
  3. washThe residue is washed with 1×25 ml dichloromethane
  4. customthe insoluble material is removed by filtration
  5. concentrationThe filtrate is concentrated in vacuo to a yellow oil
  6. customThe oil is chromatographed over 15 g silica gel (230-400 mesh)eluting with 3% methanol/dichloromethane
  7. customcollecting 6 ml fractions
  8. concentrationconcentrated
  9. customto afford a colorless oil which
  10. customis crystallized from diethyl ether

Sources & evidence

ORD record
ord-a1f7c51234f9452aacfd122174aca252
Source dataset
uspto-grants-1997_12
Patent number
US05703075

Reaction notes

Loading…