Benzyl Alcohol → Benzyl 3-oxocyclopentanecarboxylate

HRID 1024500

Reaction equation

HRID 1024500 reaction equation
[O:1]=[C:2]1[CH2:6][CH2:5][CH:4]([C:7]([OH:9])=[O:8])[CH2:3]1.[CH2:10](O)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.Cl.C(N=C=NCCCN(C)C)C.ON1C2C=CC=CC=2N=N1.C(=O)(O)[O-].[Na+]>O1CCCC1>[CH2:10]([O:8][C:7]([CH:4]1[CH2:5][CH2:6][C:2](=[O:1])[CH2:3]1)=[O:9])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

7

Reactant 5

HCID 244Benzyl AlcoholHCID 757711-HydroxybenzotriazoleHCID 2277983-Oxocyclopentanecarboxylic acidHCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 14530748Benzyl 3-oxocyclopentanecarboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The mixture of 3-oxo-cyclopentanecarboxylic acid (750 mg), of benzyl alcohol (633 mg), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride 1 (680 mg), and of 1-hydroxybenzotriazole (350 mg) in 50 ml tetrahydrofuran was stirred overnight. After addition of aq. Sodium bicarbonate (sat. 25 mL), the reaction mixture was extracted with of ethyl acetate (50 ml×2). The organic layer was washed with brine, dried with anhydrous sodium sulfate and concentrated to yield 3-oxo-cyclopentanecarboxylic acid benzyl ester as oil.

Workup

  1. extractionthe reaction mixture was extracted with of ethyl acetate (50 ml×2)
  2. washThe organic layer was washed with brine
  3. dry with materialdried with anhydrous sodium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-cb7821b47b8d410f88f1bbdc77d3fe7d
Source dataset
uspto-grants-2014_05
Patent number
US08722896B2

Linked notes

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