Potassium tert-butoxide → HCID 58197246, compound

HRID 1503419Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[CH:4][C:5](F)=[C:6]([CH:17]=1)[C:7]([C:9]1([OH:16])[CH2:14][CH2:13][C:12](=[O:15])[CH2:11][CH2:10]1)=[O:8].CC([O-])(C)C.[K+]>C1COCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[O:16][C:9]3([CH2:14][CH2:13][C:12](=[O:15])[CH2:11][CH2:10]3)[C:7](=[O:8])[C:6]=2[CH:17]=1

Participants

Conditions

Temperature: 100 °C

Procedure

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.

Workup

temperatureThe reaction mixture was then cooled with an ice bath
customquenched with H2O
extractionextracted with ethyl acetate
dry with materialdried over Na2SO4
customAfter the solvents were evaporated
customthe residue was purified by chromatography on silica gel
washeluted with hexanes/ethyl acetate

Sources & evidence

ORD record: ord-33dce48bb59743ccb6a82649bebff3d3
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09212153B2

Reaction notes

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