Hydrochloric Acid → HCID 66640348, compound

HRID 1094489Notes

Reaction equation

HRID 1094489 reaction equation
[CH2:1]([O:3][C:4](=[O:9])[CH2:5][C:6]([OH:8])=O)[CH3:2].N1C=CC=CC=1C1C=CC=CN=1.[CH3:22][O:23][C:24]([C:26]1[C:35]2[C:30](=[CH:31][C:32]([CH2:36]C(Cl)=O)=[CH:33][CH:34]=2)[CH:29]=[CH:28][CH:27]=1)=[O:25].Cl>C1COCC1.CCOCC>[CH3:22][O:23][C:24]([C:26]1[C:35]2[C:30](=[CH:31][C:32]([CH2:36][C:6](=[O:8])[CH2:5][C:4]([O:3][CH2:1][CH3:2])=[O:9])=[CH:33][CH:34]=2)[CH:29]=[CH:28][CH:27]=1)=[O:25]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14742,2'-BipyridineHCID 70615Monoethyl malonateHCID 86665165HCID 86665165, compound

Product 1

HCID 66640348HCID 66640348, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent4×

Conditions

Temperature
-10 °C

Procedure

A solution of 8.56 g (64.8 mMol) of malonic acid monoethyl ester and 112 mg (0.72 mMol) 2,2′-bipyridine in 200 ml THF is cooled to −78° C. Then 60 ml of a 1.6 M solution of nbutyllithium in THF are added dropwise (color changes from yellow to red!). Warming the mixture up to −10° C., renders the mixture turn to yellow again. Addition of another 10 ml of a 1.6 M solution of nbutyllithium in THF results in a persistent red color of the mixture. After cooling to −78° C., a suspension of 36 mMol 6-chlorocarbonylmethyl-naphthalene-1-carboxylic acid methyl ester in 250 ml THF is added during 40 min and then stirring is continued for 1 h. The dark mixture is poured into 200 ml of 1 N HCl and 400 ml ether, the aq. phase separated off and extracted with 2 portions of EtOAc. The organic layers are washed with brine, dried (Na2SO4) and concentrated to the title compound which can be used in the Step 3.6 as such. Pure product can be obtained by chromatography (Combi Flash; hexane/EtOAc 85:15): MS: [M−1]=313; HPLC: tRet=15.5.

Workup

  1. customresults in a persistent red color of the mixture
  2. temperatureAfter cooling to −78° C.
  3. additionis added during 40 min
  4. customthe aq. phase separated off
  5. extractionextracted with 2 portions of EtOAc
  6. washThe organic layers are washed with brine
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated to the title compound which
  9. customPure product can be obtained by chromatography (Combi Flash; hexane/EtOAc 85:15)

Sources & evidence

ORD record
ord-43f0cfb030f641c09ad36326e2868cb6
Source dataset
uspto-grants-2012_03
Patent number
US08133886B2

Reaction notes

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