Hydrochloric Acid → HCID 21780009, compound

HRID 420257Notes

Reaction equation

HRID 420257 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9](=[O:11])[CH3:10].Cl.[C:13]([O:16][CH2:17][CH3:18])(=[O:15])[CH3:14]>O1CCCC1>[OH:11][C:9]([C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=1[O:2][CH3:1])([CH3:10])[CH2:14][C:13]([O:16][CH2:17][CH3:18])=[O:15]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 684812'-Methoxyacetophenone

Product 1

HCID 21780009HCID 21780009, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Under argon atmosphere, 20 mL (10.7 mmol, 2 equivalent) of the solution of ethyl bromozincacetate in tetrahydrofuran obtained in Example 43 was added dropwise to a solution of 0.74 mL (5.35 mmol) of o-methoxyacetophenone in 2.75 mL of THF at 7˜10° C. The mixture was stirred at to 4˜6° C. for 4 hours. 10 mL of 1N hydrochloric acid was added dropwise at 20° C. or lower, followed by dilution with 30 mL of ethyl acetate. Then, the layers were separated. The organic layer was washed successively with 5 mL (×2) of 1N hydrochloric acid, 5 mL of water, 5 mL (×2) of an aqueous saturated sodium bicarbonate solution, and 5 mL (×2) of an aqueous saturated sodium chloride solution. After washing, the organic layer was dried with anhydrous magnesium sulfate. Concentration under reduced pressure afforded 1.43 g of the desired product (NMR yield 96%; internal standard dioxane).

Workup

  1. customThen, the layers were separated
  2. washThe organic layer was washed successively with 5 mL (×2) of 1N hydrochloric acid, 5 mL of water, 5 mL (×2) of an aqueous saturated sodium bicarbonate solution, and 5 mL (×2) of an aqueous saturated sodium chloride solution
  3. washAfter washing
  4. dry with materialthe organic layer was dried with anhydrous magnesium sulfate
  5. concentrationConcentration under reduced pressure

Sources & evidence

ORD record
ord-c9fc9a3c7df34b6586d0a5fe8fc5a31f
Source dataset
uspto-grants-2012_01
Patent number
US08093403B2

Reaction notes

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