Benzyl Bromide → HCID 14427964, compound

HRID 397461Notes

Reaction equation

HRID 397461 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%). δH (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-e18cb6d0b5a34b09ae074d9ee8bbcebc
Source dataset
uspto-grants-2003_08
Patent number
US06610700B2

Reaction notes

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