Carbon Dioxide → 5-Oxo-5,6,7,8-tetrahydronaphthalene-2-carboxylic acid

HRID 1003785노트

반응식

HRID 1003785 반응식
C1O[C:4]2([CH2:13][CH2:12][C:11]3[C:6](=[CH:7][CH:8]=[C:9](Br)[CH:10]=3)[CH2:5]2)OC1.C([Li])(C)(C)C.[C:21](=[O:23])=[O:22].C1C[O:27]CC1>>[C:5]1(=[O:27])[C:6]2[C:11](=[CH:10][C:9]([C:21]([OH:23])=[O:22])=[CH:8][CH:7]=2)[CH2:12][CH2:13][CH2:4]1

참가 물질

5

반응물 4

HCID 280Carbon DioxideHCID 8028TetrahydrofuranHCID 233778946-Bromo-2-tetralone ethylene ketalHCID 178418306HCID 178418306, 화합물

생성물 1

HCID 28184935-Oxo-5,6,7,8-tetrahydronaphthalene-2-carboxylic acid

반응 조건

온도
-78 °C

실험 절차

6-Bromo-2-tetralone ethylene ketal (2.2 g, 8.15 mmol) was dissolved in anhydrous THF (30 mL), cooled to -78° C. and treated with tert-butyllithium (12.05 mL, 20.4 mmol, 1.7M in pentane) under an atmosphere of nitrogen. After stirring for 30 minutes, anhydrous carbon dioxide gas was passed through the reaction mixture for 20 minutes at -78° C. The suspension was then allowed to warm to ambient temperature. The solution was quenched with water and acidified with 1N HCl, then extracted 2×EtOAc. The organic extracts were washed with brine, dried over Na2SO4 and concentrated in vacuo to a pale brown oil. The oily residue was applied to a silica flash chromatography column and eluted with 30%-50% EtOAC in hexanes to yield Tetralone-6-carboxylic acid, ethylene ketal 1.06 g (55%) of a slowly crystallizing solid. NMR. MS.

후처리

  1. temperatureto warm to ambient temperature
  2. customThe solution was quenched with water
  3. extractionextracted 2×EtOAc
  4. washThe organic extracts were washed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo to a pale brown oil
  7. washeluted with 30%-50% EtOAC in hexanes

출처 및 근거

ORD 기록
ord-00b2415dafc9492e8f80f27eafb3aea0
출처 데이터셋
uspto-grants-2000_04
특허 번호
US06046227

반응 노트

불러오는 중…