Water → HCID 57697469, compound

HRID 1524327Notes

Reaction equation

HRID 1524327 reaction equation
[H-].[Na+].[CH2:3]([N:10]([CH2:14][CH2:15][C:16]1[C:17](Cl)=[N:18][CH:19]=[CH:20][CH:21]=1)[CH2:11][CH2:12][OH:13])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.O>C1COCC1>[CH2:3]([N:10]1[CH2:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[N:18][C:17]=2[O:13][CH2:12][CH2:11]1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 962WaterHCID 24758Sodium hydrideHCID 86630358HCID 86630358, compound

Product 1

HCID 57697469HCID 57697469, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
80 °C

Procedure

Under a nitrogen atmosphere, to a suspension of sodium hydride (60% in oil, 0.24 g) in THF (5 mL) was added a solution of the compound (0.88 g) obtained in step 6 in THF (10 mL) at 0° C., and the mixture was stirred at 80° C. for 6 hr. The reaction mixture was cooled to 10° C., and poured into water. The resultant product was extracted with ethyl acetate. The organic layer was washed with saturated aqueous ammonium chloride solution and brine, and concentrated. The residue was purified by silica gel column chromatography (solvent gradient; 20→33% ethyl acetate/hexane) to give the title compound (0.59 g, 77%) as a colorless oil.

Workup

  1. temperatureThe reaction mixture was cooled to 10° C.
  2. extractionThe resultant product was extracted with ethyl acetate
  3. washThe organic layer was washed with saturated aqueous ammonium chloride solution and brine
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel column chromatography (solvent gradient; 20→33% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-f6c53920c8614eaa9f0c20d733b06c2d
Source dataset
uspto-grants-2015_07
Patent number
US09079907B2

Reaction notes

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