Hydrochloric Acid → diethyl(2E)-4-hydroxy-4-phenylhex-2-enedioate

HRID 420234

反応式

HRID 420234 の反応式
Br[Zn][CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5].[C:9](/[CH:17]=[CH:18]/[C:19]([O:21][CH2:22][CH3:23])=[O:20])(=[O:16])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.Cl.C(OCC)(=O)C>C1COCC1>[OH:16][C:9]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)([CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5])/[CH:17]=[CH:18]/[C:19]([O:21][CH2:22][CH3:23])=[O:20]

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 5369605Ethyl (2E)-4-oxo-4-phenyl-2-butenoateHCID 178472539HCID 178472539、化合物

生成物 1

HCID 57465814diethyl(2E)-4-hydroxy-4-phenylhex-2-enedioate収率 97%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒3 回

実験手順

Under nitrogen atmosphere, 15 mL of THF was added to 3.05 g (5 mmol, 1.0 equivalent) of (BrZnCH2COOEt.THF)2. Under argon atmosphere, a solution of 1.02 g (5 mmol) of trans-ethyl 3-benzoylacrylate in 2.5 mL of THF was added dropwise while stirring at 0˜5° C. The mixture was stirred at 20˜25° C. for 3 hours. 7.5 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, 10 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 1.42 g of the desired product (yield 97%).

後処理

  1. stirringThe mixture was stirred at 20˜25° C. for 3 hours
  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, 10 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. concentrationConcentration under reduced pressure

出典と根拠

ORDレコード
ord-545da04b6f1640fdbed71cb7e0b58c7d
出典データセット
uspto-grants-2012_01
特許番号
US08093403B2

関連ノート

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