Hydrochloric Acid → ethyl(4E)-3-hydroxy-3,5-diphenylpent-4-enoate

HRID 420232

反応式

HRID 420232 の反応式
Br[Zn][CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5].[C:9]1(/[CH:15]=[CH:16]/[C:17]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[O:18])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.Cl.C(OCC)(=O)C>C1COCC1>[OH:18][C:17]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)(/[CH:16]=[CH:15]/[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5]

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 637760ChalconeHCID 178472539HCID 178472539、化合物

生成物 1

HCID 11312495ethyl(4E)-3-hydroxy-3,5-diphenylpent-4-enoate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 mmol, 1.0 equivalent) of (BrZnCH2COOEt.THF)2. Under argon atmosphere, a solution of 1.04 g (5 mmol) of (E)-chalcone in 2.5 mL of THF was added dropwise while stirring at 0˜5° C. The mixture was stirred at 0˜5° 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 an aqueous saturated sodium chloride solution, 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 1.44 g of the desired product (yield 97%).

後処理

  1. stirringThe mixture was stirred at 0˜5° 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 an aqueous saturated sodium chloride solution, 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-5d0de3c0d033485db21d13ee4cbb6b3e
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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