Benzyl Bromide → Benzyl 3-oxocyclobutane-1-carboxylate

HRID 2104366Notes

Reaction equation

HRID 2104366 reaction equation
C(N(CC)CC)C.[CH2:8](Br)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[O:16]=[C:17]1[CH2:20][CH:19]([C:21]([OH:23])=[O:22])[CH2:18]1>O1CCCC1.C(OCC)(=O)C>[CH2:8]([O:23][C:21]([CH:19]1[CH2:20][C:17](=[O:16])[CH2:18]1)=[O:22])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 8471TriethylamineHCID 49133583-Oxocyclobutane-1-carboxylic acid

Product 1

HCID 15830669Benzyl 3-oxocyclobutane-1-carboxylate

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Triethylamine (2.0 mL) and benzyl bromide (1.2 mL) were added to a solution of 3-oxocyclobutanecarboxylic acid (J. Org. Chem., vol. 53, pp. 3841-3843 (1981)) (995 mg) in tetrahydrofuran (5.0 mL), and the mixture was stirred at room temperature for 2 hours. The reaction mixture was diluted with ethyl acetate, and was sequentially washed with 1N aqueous HCl, saturated aqueous sodium hydrogencarbonate, and saturated brine, followed by drying over sodium sulfate anhydrate. The solvent was distilled away under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:6), to thereby give the title compound (886 mg).

Workup

  1. washwas sequentially washed with 1N aqueous HCl, saturated aqueous sodium hydrogencarbonate, and saturated brine
  2. dry with materialby drying over sodium sulfate anhydrate
  3. distillationThe solvent was distilled away under reduced pressure
  4. customthe residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:6)

Sources & evidence

ORD record
ord-30e3b28a3f104f2daaf1eaca07cffa6d
Source dataset
uspto-grants-2009_08
Patent number
US07576135B2

Reaction notes

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