Hydrochloric Acid → HCID 117760308, compound

HRID 709651Notes

Reaction equation

HRID 709651 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:16]=[CH:17][C:18]=1[O:19][CH3:20])[CH:5]=[C:6]1[C:11](=[O:12])[O:10][C:9]([CH3:14])([CH3:13])[O:8][C:7]1=[O:15].[CH:21]1([Mg]Br)[CH2:23][CH2:22]1.Cl.C(=O)([O-])O.[Na+]>C1COCC1>[CH:21]1([CH:5]([C:4]2[CH:16]=[CH:17][C:18]([O:19][CH3:20])=[C:2]([OH:1])[CH:3]=2)[CH:6]2[C:11](=[O:12])[O:10][C:9]([CH3:13])([CH3:14])[O:8][C:7]2=[O:15])[CH2:23][CH2:22]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 21594638HCID 21594638, compoundHCID 178418630HCID 178418630, compound

Product 1

HCID 117760308HCID 117760308, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 5-(3-hydroxy-4-methoxybenzylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione (556 mg) in THF (10 mL) was added a 1.0 M solution of cyclopropylmagnesium bromide in THF (6.0 mL) at 0° C., and the mixture was stirred for 1 hr. 3N Hydrochloric acid (10 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 the mixture was 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 (300 mg) 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. extractionthe mixture was extracted 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-c33c84c3eb164023b027f07ac4753251
Source dataset
uspto-grants-2015_11
Patent number
US09181186B2

Reaction notes

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