Benzyl Bromide → Benzyl 3-oxocyclobutane-1-carboxylate

HRID 1392743Notes

Reaction equation

HRID 1392743 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>[O:16]=[C:17]1[CH2:20][CH:19]([C:21]([O:23][CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[O:22])[CH2:18]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 washed successively with 1N hydrochloric acid, a saturated aqueous solution of sodium hydrogencarbonate and saturated saline and dried over anhydrous sodium sulfate. The solvent was then distilled off under reduced pressure, and the resultant residue was purified by column chromatography on silica gel (ethyl acetate:hexane=1:6) to obtain the title compound (886 mg).

Workup

  1. washwashed successively with 1N hydrochloric acid
  2. dry with materiala saturated aqueous solution of sodium hydrogencarbonate and saturated saline and dried over anhydrous sodium sulfate
  3. distillationThe solvent was then distilled off under reduced pressure
  4. customthe resultant residue was purified by column chromatography on silica gel (ethyl acetate:hexane=1:6)

Sources & evidence

ORD record
ord-a624f2b04e924746a6446bbbade259ef
Source dataset
uspto-grants-2008_03
Patent number
US07342014B2

Reaction notes

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