Benzyl Bromide → HCID 14427964, compound

HRID 1837036Notes

Reaction equation

HRID 1837036 reaction equation
[C:1]1(=[O:7])[CH2:5][CH2:4][C:3](=[O:6])[CH2:2]1.[I-].[Li+].C1CCN2C(=NCCC2)CC1.[CH2:21](Br)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>C(#N)C.O>[CH2:21]([CH:2]1[C:3](=[O:6])[CH2:4][CH2:5][C:1]1=[O:7])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

7

Reactant 4

HCID 7498Benzyl BromideHCID 66321Lithium iodideHCID 774661,3-CyclopentanedioneHCID 811841,8-Diazabicyclo(5.4.0)undec-7-ene

Product 1

HCID 14427964HCID 14427964, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

To a suspension of 1,3-cyclopentanedione (500 mg, 5.10 mmol) and anhydrous lithium iodide (750 mg, 5.61 mmol) in acetonitrile (10 ml) was added DBU. After 30 min benzyl bromide (1.74 g, 10.2 mmol) was added and the reaction heated for 24 h at reflux. The reaction was poured into water (40 ml), extracted with EtOAc (4×50 ml), dried (MgSO4), the solution concentrated in vacuo and the residue purified by chromatography (SiO2; EtOAc) to give the title compound as an off white solid (222 mg, 23%). δ H (CD3OD) 7.20 (4H, d), 7.10 (1H, m), 3.41 (2H, s), 2.52 (4H, s). m/z (ESI, 70V) 189 (MH+).

Workup

  1. temperaturethe reaction heated for 24 h
  2. temperatureat reflux
  3. extractionextracted with EtOAc (4×50 ml)
  4. dry with materialdried (MgSO4)
  5. concentrationthe solution concentrated in vacuo
  6. customthe residue purified by chromatography (SiO2; EtOAc)

Sources & evidence

ORD record
ord-1163ec3e8a01469983b3571b5304f48a
Source dataset
uspto-grants-2004_08
Patent number
US06780874B2

Reaction notes

Loading…