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

HRID 527086

반응식

HRID 527086 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-24e9934f5647439ca376bdd4d797d436
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09345708B2

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