Potassium tert-butoxide → HCID 58197246, compound

HRID 473001Notes

Reaction equation

HRID 473001 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

4

Reactant 2

HCID 23665647Potassium tert-butoxideHCID 58197149HCID 58197149, compound

Product 1

HCID 58197246HCID 58197246, compoundYield 41.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

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

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

Sources & evidence

ORD record
ord-c0e14e6ba4e848daa216bb467d55c794
Source dataset
uspto-grants-2014_01
Patent number
US08633212B2

Reaction notes

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