Hydrochloric Acid → Ethyl (1-hydroxy-2,5-dimethyl-4-oxocyclohexa-2,5-dien-1-yl)acetate

HRID 1444976ノート

反応式

HRID 1444976 の反応式
Br[Zn][CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5].[CH3:9][C:10]1[C:11](=[O:18])[CH:12]=[C:13]([CH3:17])[C:14](=[O:16])[CH:15]=1.Cl.C(OCC)(=O)C>C1COCC1>[OH:18][C:11]1([CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5])[CH:12]=[C:13]([CH3:17])[C:14](=[O:16])[CH:15]=[C:10]1[CH3:9]

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 87182,5-Dimethyl-4-benzoquinoneHCID 8857Ethyl AcetateHCID 178472539HCID 178472539、化合物

生成物 1

HCID 45093815Ethyl (1-hydroxy-2,5-dimethyl-4-oxocyclohexa-2,5-dien-1-yl)acetate収率 87%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒3 回

実験手順

Under nitrogen atmosphere, 6 mL of THF was added to 1.22 g (2 mmol, 0.6 equivalent) of (BrZnCH2COOEt.THF)2. Under argon atmosphere, a solution of 0.45 g (3.33 mmol) of 2,5-dimethyl-p-benzoquinone in 3 mL of THF was added 15 dropwise while stirring at 0˜5° C. The mixture was stirred at 20˜25° C. for 1 hour. 5 mL of 1N hydrochloric acid was added dropwise at 20° C. or lower, followed by dilution with 25 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, purification with silica gel column (developing solvent; ethyl acetate/n-hexane=1/3, 1/2) afforded 0.65 g of the desired product (yield 87%).

後処理

  1. stirringThe mixture was stirred at 20˜25° C. for 1 hour
  2. customThen, the layers were separated
  3. 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
  4. washAfter washing
  5. dry with materialthe organic layer was dried with anhydrous magnesium sulfate
  6. concentrationAfter concentration
  7. customunder reduced pressure, purification with silica gel column (developing solvent; ethyl acetate/n-hexane=1/3, 1/2)

出典と根拠

ORDレコード
ord-e9d75dd7247046c88a67006c175db5be
出典データセット
uspto-grants-2010_02
特許番号
US07662974B2

反応ノート

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