Ethanol → HCID 18331373, compound

HRID 2270565Notes

Reaction equation

HRID 2270565 reaction equation
[Br:1][C:2]1[C:3]([Cl:21])=[C:4]([CH2:12][NH:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[C:5](F)=[C:6]([N+:8]([O-:10])=[O:9])[CH:7]=1.[CH2:22]([OH:24])[CH3:23].O1CCCC1.[H-].[Na+]>CCOCC.O>[Br:1][C:2]1[C:3]([Cl:21])=[C:4]([CH2:12][NH:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[C:5]([O:24][CH2:22][CH3:23])=[C:6]([N+:8]([O-:10])=[O:9])[CH:7]=1

Participants

7

Reactant 4

HCID 702EthanolHCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 18331464HCID 18331464, compound

Product 1

HCID 18331373HCID 18331373, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
0 °C

Procedure

To a mixture of the compound (200 mg) obtained in Example 519c, ethanol (36 μl) and tetrahydrofuran (5 ml), sodium hydride (content, 60%; 25 mg) was added under ice cooling. The reaction mixture was stirred at 0° C. for 2 h and then water and ether were added. The organic layer was washed with water and a saturated aqueous sodium chloride solution sequentially, then dried with anhydrous sodium sulfate and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluent, ethyl acetate:n-hexane=1:4) to give 197 mg of the titled compound (yield, 92%).

Workup

  1. additionwas added under ice cooling
  2. washThe organic layer was washed with water
  3. dry with materiala saturated aqueous sodium chloride solution sequentially, then dried with anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue was purified by silica gel column chromatography (eluent, ethyl acetate:n-hexane=1:4)

Sources & evidence

ORD record
ord-fd6b5cf2775b4ed1af2f21e11f76ad62
Source dataset
uspto-grants-2001_12
Patent number
US06331553B1

Reaction notes

Loading…