Hydrochloric Acid → HCID 57465821, compound

HRID 420255Notes

Reaction equation

HRID 420255 reaction equation
[C:1]([C:5]1[C:6]([O:17][CH3:18])=[C:7]([CH:10]=[C:11]([C:13]([CH3:16])([CH3:15])[CH3:14])[CH:12]=1)[CH:8]=[O:9])([CH3:4])([CH3:3])[CH3:2].Cl.[C:20]([O:23][CH2:24][CH3:25])(=[O:22])[CH3:21]>O1CCCC1>[C:1]([C:5]1[C:6]([O:17][CH3:18])=[C:7]([CH:8]([OH:9])[CH2:21][C:20]([O:23][CH2:24][CH3:25])=[O:22])[CH:10]=[C:11]([C:13]([CH3:16])([CH3:15])[CH3:14])[CH:12]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 40609583,5-Di-tert-butyl-2-methoxybenzaldehyde

Product 1

HCID 57465821HCID 57465821, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Under argon atmosphere, 7.5 mL (4.01 mmol, 2 equivalents) of the solution of ethyl bromozincacetate in terahydrofuran obtained in Example 43 was added dropwise to a solution of 0.5 g (2.01 mmol) of 3,5-di-tert-butyl-2-methoxybenzaldehyde in 5 mL of THF at 5˜7° C. The mixture was stirred at 5˜7° C. for 4 hours. 5 mL of 1N hydrochloric acid was added dropwise at 20° C. or lower, followed by dilution with 15 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. After concentration under reduced pressure, crystals were loosened with 4 mL of n-hexane to obtain 0.58 g of the desired product (yield 86%).

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. concentrationAfter concentration under reduced pressure, crystals

Sources & evidence

ORD record
ord-d33d11bed9e54557aa273490eba24721
Source dataset
uspto-grants-2012_01
Patent number
US08093403B2

Reaction notes

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