반응 #423749

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4-(5-bromo-2-fluorobenzoyl)-4-hydroxycyclohexanone

t-BuOK

→

5-bromo-3H-spiro[benzofuran-2,1′-cyclohexane]-3,4′-dione

수율 41.3%

용매

THF

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후처리

1. 1
   온도The reaction mixture was then cooled with an ice bath
2. 2
   기타quenched with H2O
3. 3
   추출extracted with ethyl acetate
4. 4
   건조dried over Na2SO4
5. 5
   기타After the solvents were evaporated
6. 6
   기타the residue was purified by chromatography on silica gel
7. 7
   세척eluted with hexanes/ethyl acetate

실험 절차

To a solution of 4-(5-bromo-2-fluorobenzoyl)-4-hydroxycyclohexanone (1.0055 g, 3.19 mmol, 1.0 equiv) in THF (30 mL) was added 95% t-BuOK (0.3440 g, 2.91 mmol, 0.9 equiv) portionwise. The resulting mixture was heated at 100° C. for 1 h. The reaction mixture was then cooled with an ice bath and quenched with H2O, extracted with ethyl acetate, dried over Na2SO4. After the solvents were evaporated, the residue was purified by chromatography on silica gel eluted with hexanes/ethyl acetate to afford 0.3889 g (41%) of 5-bromo-3H-spiro[benzofuran-2,1′-cyclohexane]-3,4′-dione as a white solid. LC-MS tR=1.58 min in 3 min chromatography, m/z 295, 297 (MH+); 1H NMR (400 MHz, CDCl3) δ 7.82-7.81 (m, 1H), 7.76-7.73 (m, 1H), 7.10-7.07 (m, 1H), 2.81-2.72 (m, 2H), 2.60-2.55 (m, 2H), 2.29-2.21 (m, 2H), 2.08-2.03 (m, 2H); 13C NMR (100 MHz, CDCl3) δ 208.25, 200.80, 169.71, 140.99, 127.47, 121.58, 115.55, 114.81, 88.10, 36.68, 31.86.

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