Water → Benzyl 3-oxocyclopentanecarboxylate

HRID 1160607

반응식

HRID 1160607 반응식
[C:1]([CH:4]1[CH2:8][CH2:7][C:6](=[O:9])[CH2:5]1)([OH:3])=[O:2].C(=O)([O-])[O-].[K+].[K+].[CH2:16](Br)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.O>CN(C=O)C>[O:9]=[C:6]1[CH2:7][CH2:8][CH:4]([C:1]([O:3][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[O:2])[CH2:5]1

참가 물질

6

반응물 4

HCID 962WaterHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 2277983-Oxocyclopentanecarboxylic acid

생성물 1

HCID 14530748Benzyl 3-oxocyclopentanecarboxylate

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of 3-carboxycyclopentanone (640 mg, 5.0 mmol) in 8 mL of degassed DMF was added potassium carbonate (828 mg, 5.99 mmol) and benzyl bromide (0.65 mL, 5.49 mmol). After 4 hours at room temperature, the reaction mixture was poured into 50 mL of water and extracted 3 times with EtOAc. The combined organic layers were washed with water and dried over sodium sulfate. Filtration and solvent removal provided material that was subjected to silica gel chromatography eluting with 10% EtOAc in hexanes to yield benzyl 3-oxocyclopentanecarboxylate.

후처리

  1. extractionextracted 3 times with EtOAc
  2. washThe combined organic layers were washed with water
  3. dry with materialdried over sodium sulfate
  4. filtrationFiltration and solvent removal
  5. customprovided material that
  6. washeluting with 10% EtOAc in hexanes

출처 및 근거

ORD 기록
ord-850faf859de6495bbc7ecf00d17421a9
출처 데이터셋
uspto-grants-2010_10
특허 번호
US07816380B2

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