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Dimethylformamide → 7-Hydroxy-6-(4-(quinolin-2-ylmethoxy)phenyl)-4-oxaspiro[2.4]hept-6-en-5-one

HRID 655383
ノート
印刷プレビュー

反応式

HRID 655383 の反応式
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([CH2:19][C:20]([O:22][C:23]2([C:26]([O:28]C)=O)[CH2:25][CH2:24]2)=[O:21])=[CH:15][CH:14]=1.CN(C=O)C>>[OH:28][C:26]1[C:23]2([CH2:25][CH2:24]2)[O:22][C:20](=[O:21])[C:19]=1[C:16]1[CH:15]=[CH:14][C:13]([O:12][CH2:11][C:2]2[CH:3]=[CH:4][C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[N:1]=2)=[CH:18][CH:17]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

3

反応物 2

HCID 6228DimethylformamideHCID 59354788HCID 59354788、化合物

生成物 1

HCID 593548297-Hydroxy-6-(4-(quinolin-2-ylmethoxy)phenyl)-4-oxaspiro[2.4]hept-6-en-5-one収率 83%

実験手順

To a 0° C. solution of methyl 1-(2-(4-(quinolin-2-ylmethoxy)phenyl)acetoxy)cyclopropanecarboxylate (2.0 g, 6.825 mmol) in DMF (20 mL) NaH (49 mg, 20.477 mol) was added and the mixture stirred at RT for 12 h. After complete consumption of the starting material (by TLC), the reaction mixture was quenched with ice water (3 mL) and the aqueous layer was extracted with EtOAc (2×50 mL). The combined organic layers were washed with water (30 mL) and brine (20 mL), dried over anhydrous Na2SO4, filtered, and concentrated in vacuo to afford crude 7-hydroxy-6-(4-(quinolin-2-ylmethoxy)phenyl)-4-oxaspiro[2.4]hept-6-en-5-one (2.0 g, 83%) as a light yellow color solid.

後処理

  1. custom
After complete consumption of the starting material (by TLC)
  • customthe reaction mixture was quenched with ice water (3 mL)
  • extractionthe aqueous layer was extracted with EtOAc (2×50 mL)
  • washThe combined organic layers were washed with water (30 mL) and brine (20 mL)
  • dry with materialdried over anhydrous Na2SO4
  • filtrationfiltered
  • concentrationconcentrated in vacuo
  • 出典と根拠

    ORDレコード
    ord-d62dc73d3ac643d5a4f953049a20d45e
    出典データセット
    uspto-grants-2011_12
    DOI
    10.6084/m9.figshare.5104873.v1
    特許番号
    US08071595B2

    反応ノート

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