Hydrochloric Acid → 6-Oxobicyclo[2.2.1]heptane-2-carboxylic acid

HRID 75045

반응식

HRID 75045 반응식
Br[CH:2]1[CH:6]2[O:7][C:8](=[O:11])[CH:9]3[CH2:10][CH:3]1[CH2:4][CH:5]23.[OH-:12].[Na+].Cl>O>[O:12]=[C:6]1[CH:5]2[CH2:4][CH:3]([CH2:10][CH:9]2[C:8]([OH:7])=[O:11])[CH2:2]1

참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 2636406-Bromohexahydro-2h-3,5-methanocyclopenta[b]furan-2-one2회

생성물 1

HCID 3619876-Oxobicyclo[2.2.1]heptane-2-carboxylic acid

시약·촉매·용매 1

HCID 962Water용매

실험 절차

6-bromohexahydro-2H-3,5-methanocyclopenta[b]furan-2-one, 72a, (28.0 g, 129.0 mmol) was treated with NaOH (258.0 mL of 2 M solution, 516.0 mmol) in H2O (350 mL) for 2 hour at room temperature. The reaction mixture was acidified with conc. HCl, extracted with Et2O. The organic phase was dried (Na2SO4), filtered and concentrated in vacuo. The resulting residue was purified by silica gel chromatography (0-20% MeOH/CH2Cl2 gradient) to provide 16 g of 6-oxonorbornane-2-carboxylic acid.

후처리

  1. extractionextracted with Et2O
  2. dry with materialThe organic phase was dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe resulting residue was purified by silica gel chromatography (0-20% MeOH/CH2Cl2 gradient)

출처 및 근거

ORD 기록
ord-6f647d28975e474788537356a75bd018
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08829007B2

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