Water → HCID 57697469, compound

HRID 1692599Notes

Reaction equation

HRID 1692599 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-b59d033902ff4143bd56aa0fd0710a0a
Source dataset
uspto-grants-2012_04
Patent number
US08158617B2

Reaction notes

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