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

HRID 567999

反応式

HRID 567999 の反応式
[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

参加物

7

反応物 4

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

生成物 1

HCID 3048321,3-Dioxaindane-4-carboxylic acid

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒2 回HCID 8058Hexane溶媒

実験手順

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)+.

後処理

  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%)

出典と根拠

ORDレコード
ord-ccaca81eba15407fac63fc44cfd8354c
出典データセット
uspto-grants-2001_01
特許番号
US06180675B2

関連ノート

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