Tetrahydrofuran → HCID 67224735, compound

HRID 500144Notes

Reaction equation

HRID 500144 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][C:7]([OH:11])=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.C[Si](C)(C)N[Si](C)(C)C.[Na].C1COCC1.Br[CH2:28][CH:29]([O:32][CH3:33])[O:30][CH3:31]>CN(C)C=O>[CH3:31][O:30][CH:29]([O:32][CH3:33])[CH2:28][O:11][C:7]1[CH:6]=[C:5]2[C:10](=[CH:9][CH:8]=1)[N:1]=[CH:2][CH:3]=[CH:4]2

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 113746-HydroxyquinolineHCID 816722-Bromo-1,1-dimethoxyethaneHCID 45051731Sodium hexamethyidisilazane

Product 1

HCID 67224735HCID 67224735, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a cooled (0° C.) solution of quinolin-6-ol (5.81 g, 40 mmol) in N,N-dimethylformamide (30 mL) was slowly added a 1M solution of sodium hexamethyldisilazane in THF (40 mL, 40 mmol). The mixture was stirred for 15 min after which 2-bromo-1,1-dimethoxyethane (5.18 mL, 44 mmol) was added. The reaction mixture was then refluxed conditions for 6 h. The solvent was evaporated under reduced pressure. The residue was diluted with diethyl ether (100 mL) and washed with water, brine, dried over sodium sulfate, filtered, and concentrated. The residue was purified by flash chromatography eluting with ethyl acetate in hexanes. (0-50%) to give the desired product. (9 g, 96%) LCMS: (M+H)+=233.9.

Workup

  1. additionwas added
  2. customThe solvent was evaporated under reduced pressure
  3. additionThe residue was diluted with diethyl ether (100 mL)
  4. washwashed with water, brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by flash chromatography
  9. washeluting with ethyl acetate in hexanes

Sources & evidence

ORD record
ord-0e0b0e7ee049411c81b5713696f47e35
Source dataset
uspto-grants-2010_08
Patent number
US07767675B2

Reaction notes

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