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

HRID 1258266
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HRID 1258266 반응식
[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
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

3

반응물 2

HCID 6228DimethylformamideHCID 59354788HCID 59354788, 화합물

생성물 1

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

실험 절차

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.

후처리

  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
  • 출처 및 근거

    ORD 기록
    ord-16e3a822daf64a26abc19e4d5c127284
    출처 데이터셋
    uspto-grants-2013_06
    DOI
    10.6084/m9.figshare.5104873.v1
    특허 번호
    US08466148B2

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