Sodium hydride → HCID 86616640, compound

HRID 1992830Notes

Reaction equation

HRID 1992830 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9]([OH:13])=[C:8]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:7]([CH3:20])=[CH:6]2.[H-].[Na+].[F:23][C:24]1[CH:25]=[C:26]([CH:29]=[CH:30][C:31]=1F)[CH:27]=[O:28]>CN(C=O)C>[F:23][C:24]1[CH:25]=[C:26]([CH:29]=[CH:30][C:31]=1[O:13][C:9]1[C:10]2[C:5](=[CH:4][C:3]([O:2][CH3:1])=[CH:12][CH:11]=2)[CH:6]=[C:7]([CH3:20])[C:8]=1[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)[CH:27]=[O:28]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 5880883,4-DifluorobenzaldehydeHCID 685363886-Methoxy-3-methyl-2-phenyl-1-naphthol

Product 1

HCID 86616640HCID 86616640, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

Compound 7 (204 mg, 0.77 mmol, 1 equiv) was dissolved in DMF (5 mL) and cooled to 0° C. under N2. Sodium hydride, 60% dispersion (34 mg, 0.85 mmol, 1.1 equiv), followed by 3,4-difluorobenzaldehyde (170 μL, 1.54 mmol, 2 equiv) were added and the entire reaction mixture was heated to 70° C. for 2 days. The mixture was then partitioned between EtOAc (50 mL) and H2O (50 mL). The organic layer was washed with saturated aqueous NaCl (100 mL), dried over Na2SO4, filtered and concentrated to dryness. The residue was purified by silica gel flash column chomatography (5% EtOAc in hexanes) to provide 24 (103 mg, 44%) as a clear oil. 1HNMR (400 MHz, DMSO-d6): δ 9.75 (s, 1H), 7.77 (s, 1H), 7.63 (m, 1H), 7.58 (d, J=9.2 Hz, 1H), 7.47 (m, 1H), 7.38 (m, 1H), 7.31-7.17 (m, 5H), 7.12 (dd, J=2.3, 8.9 Hz, 1H), 6.58 (t, J=7.3, 8.9 Hz, 1H), 3.87 (s, 3H), 2.19 (s, 3H). MS m/z 463.3 (M−H)−.

Workup

  1. additionwere added
  2. customthe entire reaction mixture
  3. temperaturewas heated to 70° C. for 2 days
  4. customThe mixture was then partitioned between EtOAc (50 mL) and H2O (50 mL)
  5. washThe organic layer was washed with saturated aqueous NaCl (100 mL)
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated to dryness
  9. customThe residue was purified by silica gel flash column chomatography (5% EtOAc in hexanes)

Sources & evidence

ORD record
ord-7024718b4ef54888a129030051881c3e
Source dataset
uspto-grants-2010_01
Patent number
US07649093B2

Reaction notes

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