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Benzaldehyde → Diethyl 4-hydroxy-4-phenyl-1,3-butanedicarboxylate

HRID 263691
ノート
印刷プレビュー

反応式

HRID 263691 の反応式
[C:1]([O:11][CH2:12][CH3:13])(=[O:10])[CH2:2][CH2:3][CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6].[CH:14](=[O:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C1CCCCC1.C([N-]C(C)C)(C)C.[Li+].[Cl-].[NH4+]>O1CCCC1>[OH:21][CH:14]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH:4]([C:5]([O:7][CH2:8][CH3:9])=[O:6])[CH2:3][CH2:2][C:1]([O:11][CH2:12][CH3:13])=[O:10]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 240BenzaldehydeHCID 13163Diethyl glutarateHCID 25517Ammonium ChlorideHCID 86604122LDA cyclohexane

生成物 1

HCID 19038618Diethyl 4-hydroxy-4-phenyl-1,3-butanedicarboxylate収率 51.1%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

2.0 g of diethyl glutarate and 1.1 g of benzaldehyde were dissolved in 30 ml of tetrahydrofuran, and 8.5 ml of a 1.5M lithium diisopropylamide cyclohexane solution was dropwise added thereto at -78° C. under a nitrogen atmosphere, followed by stirring at the same temperature for 1.5 hours. A saturated ammonium chloride aqueous solution was added to the reaction solution, and the mixture was extracted with ethyl acetate. Then, the organic layer was washed with a saturated sodium chloride aqueous solution and dried over anhydrous magnesium sulfate. The drying agent was filtered off, and then, the solvent was distilled off under reduced pressure. The residue was purified by medium pressure liquid chromatography (Lobar column™, size C, Lichroprep™Si60, manufactured by Merck Co.; hexane/ethyl acetate=3/1) to obtain 1.56 g of the above-identified compound as colorless oily substance.

後処理

  1. customat -78° C.
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThen, the organic layer was washed with a saturated sodium chloride aqueous solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationThe drying agent was filtered off
  6. distillationthe solvent was distilled off under reduced pressure
  7. customThe residue was purified by medium pressure liquid chromatography (Lobar column™, size C, Lichroprep™Si60, manufactured by Merck Co.; hexane/ethyl acetate=3/1)

出典と根拠

ORDレコード
ord-5067783538904fa39aa80e1401fbaffa
出典データセット
uspto-grants-1997_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05643958

反応ノート

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