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

HRID 527086

反応式

HRID 527086 の反応式
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

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 2636406-Bromohexahydro-2h-3,5-methanocyclopenta[b]furan-2-one2 回

生成物 1

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

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-24e9934f5647439ca376bdd4d797d436
出典データセット
uspto-grants-2016_05
特許番号
US09345708B2

関連ノート

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