Hydrochloric Acid → HCID 59516813, compound

HRID 1698706Notes

Reaction equation

HRID 1698706 reaction equation
[F:1][C:2]1[C:7]2[CH2:8][CH2:9][O:10][C:6]=2[C:5]([O:11][CH3:12])=[CH:4][CH:3]=1.C([Li])CCC.[CH:18](N1CCOCC1)=[O:19].Cl>C1COCC1>[F:1][C:2]1[C:7]2[CH2:8][CH2:9][O:10][C:6]=2[C:5]([O:11][CH3:12])=[CH:4][C:3]=1[CH:18]=[O:19]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 20417N-FormylmorpholineHCID 59517096HCID 59517096, compoundHCID 178418339Butyllithium

Product 1

HCID 59516813HCID 59516813, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-74 °C

Procedure

To a solution of 665 mg of 4-fluoro-7-methoxy-2,3-dihydrobenzofuran and 740 mg of N,N,N′,N,N″-pentamethyldiethylenetriamine in 15 ml of THF there was added dropwise 1.66 ml of n-butyllithium (2.55 M, hexane solution) at −74° C. The mixture was stirred at −74° C. for 1 hour, and then 500 μl of N-formylmorpholine was added. After further stirring at room temperature for 1 hour, 1N hydrochloric acid was added to the reaction mixture while cooling on ice, and the mixture was extracted with ethyl acetate and dried over anhydrous magnesium sulfate. The desiccating agent was filtered off and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate-heptane) to give the title compound (321 mg) as an oil.

Workup

  1. stirringAfter further stirring at room temperature for 1 hour
  2. temperaturewhile cooling on ice
  3. extractionthe mixture was extracted with ethyl acetate
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationThe desiccating agent was filtered off
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (ethyl acetate-heptane)

Sources & evidence

ORD record
ord-9c39717638d6470c98aa7a2064f3b0e0
Source dataset
uspto-grants-2012_04
Patent number
US08163787B2

Reaction notes

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