Carbon Dioxide → 3-(2-Formylphenyl)benzo[d]isoxazole-6-carboxylic acid

HRID 475429노트

반응식

HRID 475429 반응식
Br[C:2]1[CH:23]=[CH:22][C:5]2[C:6]([C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[CH:15]([O:19]CC)OCC)=[N:7][O:8][C:4]=2[CH:3]=1.C([Li])CCC.[C:29](=[O:31])=[O:30]>CCOCC>[CH:15]([C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=1[C:6]1[C:5]2[CH:22]=[CH:23][C:2]([C:29]([OH:31])=[O:30])=[CH:3][C:4]=2[O:8][N:7]=1)=[O:19]

참가 물질

5

반응물 3

HCID 280Carbon Dioxide2회HCID 66847930HCID 66847930, 화합물2회HCID 178418339Butyllithium

생성물 1

HCID 867622653-(2-Formylphenyl)benzo[d]isoxazole-6-carboxylic acid

시약·촉매·용매 1

HCID 3283Diethyl Ether용매2회

실험 절차

To a solution of 6-bromo-3-(2-(diethoxymethyl)phenyl)benzo[d]isoxazole (Compound 5) (50 g) in dry ether (330 mL) under nitrogen at −78° C. was added a 2.5M solution of n-butyl lithium in hexanes (55.8 mL) was added dropwise and stirring continued at −78° C. for 45 min. The thick brown suspension was transferred via cannula to a mechanically stirred mixture of solid carbon dioxide pellets in ether (250 mL, under nitrogen and cooled in acetone/dry ice bath) and the resulting reaction mix topped up with further carbon dioxide pellets and left stirring in cold bath under nitrogen whilst warming to room temperature overnight. The reaction was quenched with 2N HCl (100 mL) and the ether removed under reduced pressure and ethanol (300 mL) added. The resultant yellow suspension was stirred on at 60° C. for 15 min, then cooled to room temperature and stirred in ice bath for 30 min and resulting yellow solid isolated by filtration and dried in vacuum oven at 45° C. to give the title product (29.76 g).

후처리

  1. additionwas added dropwise
  2. customthe resulting reaction
  3. additionmix
  4. waitleft
  5. stirringstirring in cold bath under nitrogen
  6. customThe reaction was quenched with 2N HCl (100 mL)
  7. customthe ether removed under reduced pressure and ethanol (300 mL)
  8. additionadded
  9. stirringThe resultant yellow suspension was stirred on at 60° C. for 15 min
  10. temperaturecooled to room temperature
  11. stirringstirred in ice bath for 30 min
  12. customresulting yellow solid
  13. customisolated by filtration
  14. customdried in vacuum oven at 45° C.

출처 및 근거

ORD 기록
ord-126e6f68599c401694cbd3ab65471aad
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08637551B2

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