반응 #487587

반응 방정식

ethyl 2-(5-oxo-6,7,8,9-tetrahydro-5H-benzo[7]annulen-6-yl)acetate

potassium hydroxide

→

2-(5-oxo-6,7,8,9-tetrahydro-5H-benzo[7]annulen-6-yl)acetic acid

용매

ethanol

반응 조건

후처리

1. 1
   온도the resulting mixture was refluxed for 2 h
2. 2
   기타the EtOH was removed by evaporation
3. 3
   추출The residue was extracted with EtOAc twice (15 mL×2)
4. 4
   기타The aqueous layer was then transferred into a flask
5. 5
   온도cooled with an ice-water bath
6. 6
   workup.ADDITIONHCl was added dropwise
7. 7
   workup.ADDITIONEtOAc (60 mL) was then added
8. 8
   기타the layers were separated
9. 9
   추출the aqueous layer was extracted with EtOAc
10. 10
    세척The combined extracts were washed with brine
11. 11
    건조After being dried (MgSO4)
12. 12
    여과filtered
13. 13
    농축concentrated

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+).

출처