Potassium Hydroxide → 6,7,8,9-Tetrahydro-5-oxo-5H-benzocycloheptene-6-acetic acid

HRID 252907노트

반응식

HRID 252907 반응식
[O:1]=[C:2]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[CH2:6][CH2:5][CH2:4][CH:3]1[CH2:13][C:14]([O:16]CC)=[O:15].[OH-].[K+]>C(O)C>[O:1]=[C:2]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[CH2:6][CH2:5][CH2:4][CH:3]1[CH2:13][C:14]([OH:16])=[O:15]

참가 물질

4

반응물 2

HCID 14797Potassium HydroxideHCID 592956445H-Benzocycloheptene-6-acetic acid, 6,7,8,9-tetrahydro-5-oxo-, ethyl ester

생성물 1

HCID 3445076,7,8,9-Tetrahydro-5-oxo-5H-benzocycloheptene-6-acetic acid

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

The compound of formula (Db), ethyl 2-(5-oxo-6,7,8,9-tetrahydro-5H-benzo[7]annulen-6-yl)acetate, (6.6 g, 26.8 mmol) was dissolved in ethanol (EtOH) (30 mL), then 10% potassium hydroxide (KOH) aqueous solution (37.5 mL, 67 mmol) was added and the resulting mixture was refluxed for 2 h. After cooling to ambient temperature, the EtOH was removed by evaporation. The residue was extracted with EtOAc twice (15 mL×2). The aqueous layer was then transferred into a flask and cooled with an ice-water bath, con. HCl was added dropwise to adjust pH to about 2.0. EtOAc (60 mL) was then added, the layers were separated, and the aqueous layer was extracted with EtOAc. The combined extracts were washed with brine. After being dried (MgSO4), filtered, and concentrated, the compound of formula (Dc), 2-(5-oxo-6,7,8,9-tetrahydro-5H-benzo[7]annulen-6-yl)acetic acid, was obtained as an orange oil (5.7 g, 97%); 1H NMR (300 MHz, CDCl3) δ: 7.71-7.68 (m, 1H), 7.41-7.20 (m, 3H), 3.37-3.31 (m, 1H), 3.12-2.91 (m, 3H), 2.57-2.49 (m, 1H), 2.15-1.90 (m, 2H), 1.75-1.62 (m, 2H); LC-MS: purity: 100%; MS (m/e): 219 (MH+).

후처리

  1. temperaturethe resulting mixture was refluxed for 2 h
  2. customthe EtOH was removed by evaporation
  3. extractionThe residue was extracted with EtOAc twice (15 mL×2)
  4. customThe aqueous layer was then transferred into a flask
  5. temperaturecooled with an ice-water bath
  6. additionHCl was added dropwise
  7. additionEtOAc (60 mL) was then added
  8. customthe layers were separated
  9. extractionthe aqueous layer was extracted with EtOAc
  10. washThe combined extracts were washed with brine
  11. dry with materialAfter being dried (MgSO4)
  12. filtrationfiltered
  13. concentrationconcentrated

출처 및 근거

ORD 기록
ord-12c56ceb30ad4366bde5836a041fff14
출처 데이터셋
uspto-grants-2011_01
특허 번호
US07872000B2

반응 노트

불러오는 중…