Sodium hydride → HCID 66718591, compound

HRID 1690805Notes

Reaction equation

HRID 1690805 reaction equation
[H-].[Na+].[CH2:3]([O:10][CH2:11][CH:12]([O:15][C:16]1[C:17](Cl)=[N:18][C:19]([C:22]([F:25])([F:24])[F:23])=[CH:20][CH:21]=1)[CH2:13][OH:14])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.C([O-])(O)=O.[Na+]>COCCOC>[CH2:3]([O:10][CH2:11][CH:12]1[CH2:13][O:14][C:17]2=[N:18][C:19]([C:22]([F:25])([F:24])[F:23])=[CH:20][CH:21]=[C:16]2[O:15]1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 516892Sodium BicarbonateHCID 86650227HCID 86650227, compound

Product 1

HCID 66718591HCID 66718591, compoundYield 44.6%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent2×

Procedure

To a stirred suspension of sodium hydride (75 mg, 3.1 mmol) in anhydrous 1,2-dimethoxyethane (30 mL) was added a solution of 3-(benzyloxy)-2-(2-chloro-6-(trifluoromethyl)pyridine-3-yloxy)propan-1-ol (1.13 g, 3.1 mmol) in anhydrous 1,2-dimethoxyethane (30 mL), dropwise over 5 minutes. The reaction was heated at reflux for 90 minutes, then allowed to cool. The reaction mixture was poured into saturated NaHCO3 solution (50 mL) and extracted with EtOAc (3×30 mL). The combined organics were washed with brine (3×30 mL), dried (MgSO4), filtered and concentrated. Flash chromatography (0 to 20% EtOAc in hexanes) gave the title compound (450 mg, 43%) as an oil. m/z=325.6 (M+1), r.t.=3.46 mins. 1H NMR (400 MHz; CDCl3) 57.36-7.25 (7H, m), 4.62 (2H, d), 4.60-4.53 (1H, m, 4.43 (1H, dd), 4.18 (1H, dd), 3.87 (1H, dd), 3.74 (1H, dd).

Workup

  1. temperatureThe reaction was heated
  2. temperatureat reflux for 90 minutes
  3. temperatureto cool
  4. extractionextracted with EtOAc (3×30 mL)
  5. washThe combined organics were washed with brine (3×30 mL)
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-833a132ef395435ea3b624594ab617eb
Source dataset
uspto-grants-2012_04
Patent number
US08153651B2

Reaction notes

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