Lithium Hydroxide → Bicyclo[3.2.1]octane-1,5-dicarboxylic acid

HRID 1408854노트

반응식

HRID 1408854 반응식
C[O:2][C:3]([C:5]12[CH2:12][C:9]([C:13]([O:15]C)=[O:14])([CH2:10][CH2:11]1)[CH2:8][CH2:7][CH2:6]2)=[O:4].[OH-].[Li+]>O1CCCC1.O>[C:9]12([C:13]([OH:15])=[O:14])[CH2:12][C:5]([C:3]([OH:4])=[O:2])([CH2:11][CH2:10]1)[CH2:6][CH2:7][CH2:8]2

참가 물질

5

반응물 2

HCID 3939Lithium HydroxideHCID 13633976Dimethyl bicyclo[3.2.1]octane-1,5-dicarboxylate

생성물 1

HCID 18767672Bicyclo[3.2.1]octane-1,5-dicarboxylic acid

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

반응 조건

온도
70 °C

실험 절차

A solution of bicyclo[3.2.1]octane-1,5-dicarboxylic acid dimethyl ester (crude 3.01 g from step 2) in tetrahydrofuran (100 mL) was treated with 1 M of lithium hydroxide in water (75 mL) and warmed at 70° C. for 6 hours. The reaction was concentrated under reduced pressure and the resulting residue was partitioned between water and ethyl acetate. The aqueous layer was collected and washed again with ethyl acetate. The aqueous layer was acidified with 1N HCl to pH 2, and then extracted with ethyl acetate. The organic layer was collected, dried over anhydrous sodium sulfate, filtered, and evaporated to afford 725 mg of white solid, which was used in the next step without further purification.

후처리

  1. concentrationThe reaction was concentrated under reduced pressure
  2. customthe resulting residue was partitioned between water and ethyl acetate
  3. customThe aqueous layer was collected
  4. washwashed again with ethyl acetate
  5. extractionextracted with ethyl acetate
  6. customThe organic layer was collected
  7. dry with materialdried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. customevaporated

출처 및 근거

ORD 기록
ord-818bc899fc184facbf9007cc5f5917a1
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08921370B2

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