Carbon Dioxide → 1,3-Dioxaindane-4-carboxylic acid

HRID 567999

반응식

HRID 567999 반응식
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[O:3][CH2:2]1.C([Li])CCC.[C:15](=[O:17])=[O:16].C([O-])(O)=O.[Na+]>CCOCC.CCCCCC>[CH2:2]1[O:3][C:4]2[C:5](=[C:6]([C:15]([OH:17])=[O:16])[CH:7]=[CH:8][CH:9]=2)[O:1]1

참가 물질

7

반응물 4

HCID 280Carbon DioxideHCID 92291,3-BenzodioxoleHCID 516892Sodium BicarbonateHCID 178418339Butyllithium

생성물 1

HCID 3048321,3-Dioxaindane-4-carboxylic acid

시약·촉매·용매 2

HCID 3283Diethyl Ether용매2회HCID 8058Hexane용매

실험 절차

A solution of 1,3-benzodioxole (3.09 g, 32 mmol) in dry ether (50 mL) was treated dropwise at −10° C. with 2.5 M n-butyllithium (15 mL, 35 mmol) in hexane. When the addition was complete, the mixture was stirred under reflux for one hour. After cooling to room temperature, it was added to crushed solid carbon dioxide, and after 24 hours, the residue was treated with 10% aq. NaHCO3 and ether. The alkali layer was separated, washed with ether, then acidified with cold concentrated HCl, and extracted with chloroform. The combined organic layers were dried over MgSO4, filtered and concentrated under reduced pressure (1.1 g, 20%). EI-MS m/z 167 (M+H)+.

후처리

  1. additionWhen the addition
  2. temperatureunder reflux for one hour
  3. additionit was added
  4. customThe alkali layer was separated
  5. washwashed with ether
  6. extractionextracted with chloroform
  7. dry with materialThe combined organic layers were dried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure (1.1 g, 20%)

출처 및 근거

ORD 기록
ord-ccaca81eba15407fac63fc44cfd8354c
출처 데이터셋
uspto-grants-2001_01
특허 번호
US06180675B2

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