Hydrochloric Acid → HCID 117759790, compound

HRID 709666Notes

Reaction equation

HRID 709666 reaction equation
[F:1][C:2]1[CH:18]=[CH:17][C:5]([CH:6]=[C:7]2[C:12](=[O:13])[O:11][C:10]([CH3:15])([CH3:14])[O:9][C:8]2=[O:16])=[CH:4][C:3]=1[O:19][CH3:20].[CH:21]1([Mg]Br)[CH2:23][CH2:22]1.Cl.C(=O)([O-])O.[Na+]>C1COCC1>[CH:21]1([CH:6]([C:5]2[CH:17]=[CH:18][C:2]([F:1])=[C:3]([O:19][CH3:20])[CH:4]=2)[CH:7]2[C:8](=[O:16])[O:9][C:10]([CH3:15])([CH3:14])[O:11][C:12]2=[O:13])[CH2:23][CH2:22]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 117760111HCID 117760111, compoundHCID 178418630HCID 178418630, compound

Product 1

HCID 117759790HCID 117759790, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Under an argon atmosphere, to a solution of (5-(4-fluoro-3-methoxybenzylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione (3.00 g) in THF (20 mL) was added dropwise a 1.0 M solution of cyclopropylmagnesium bromide in THF (53.5 mL) at 0° C., and the mixture was stirred for 1 hr. 3N Hydrochloric acid (30 mL) was added to the reaction mixture, and the mixture was stirred for 15 min. The reaction mixture was neutralized with saturated aqueous sodium hydrogen carbonate solution, and extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to give the title compound (2.40 g) as a yellow solid. This compound was used for the next step without further purification.

Workup

  1. stirringthe mixture was stirred for 15 min
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-38320c4659534efca75de1e601fae277
Source dataset
uspto-grants-2015_11
Patent number
US09181186B2

Reaction notes

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