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Sulfuric Acid → 2-[6-Methoxy-4-(2-methyl-quinolin-3-yloxy)-quinolin-7-yloxymethyl]-propane-1,3-diol

HRID 228988
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HRID 228988 반응식
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[OH:13])[N:9]=[CH:8][CH:7]=[C:6]2[O:14][C:15]1[C:16]([CH3:25])=[N:17][C:18]2[C:23]([CH:24]=1)=[CH:22][CH:21]=[CH:20][CH:19]=2.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(N=C=NN=NN=C=NCC)C.S(=O)(=O)(O)O.[OH-].[Na+].CC1(C)[O:70][CH2:69][CH:68]([CH2:71]O)[CH2:67][O:66]1>O1CCCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH2:71][CH:68]([CH2:69][OH:70])[CH2:67][OH:66])[N:9]=[CH:8][CH:7]=[C:6]2[O:14][C:15]1[C:16]([CH3:25])=[N:17][C:18]2[C:23]([CH:24]=1)=[CH:22][CH:21]=[CH:20][CH:19]=2
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참가 물질

8

반응물 6

HCID 1118Sulfuric AcidHCID 11776TriphenylphosphineHCID 14798Sodium HydroxideHCID 3584869(2,2-Dimethyl-1,3-dioxan-5-yl)methanolHCID 86605188DiethylazocarbodiimideHCID 1358548286-Methoxy-4-(2-methyl-quinolin-3-yloxy)-quinolin-7-ol2회

생성물 1

HCID 57756593
2-[6-Methoxy-4-(2-methyl-quinolin-3-yloxy)-quinolin-7-yloxymethyl]-propane-1,3-diol
수율 45.8%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

6-Methoxy-4-(2-methyl-quinolin-3-yloxy)-quinolin-7-ol (compound 352) (50 mg) and triphenylphosphine (158 mg) were dissolved in tetrahydrofuran (1 ml) to prepare a solution. A solution of diethylazocarbodiimide (105 mg) in (2,2-dimethyl[1,3]dioxan-5-yl)-methanol (27 mg) and tetrahydrofuran (0.2 ml) was added to the solution, and the mixture was stirred at room temperature for 5 hr. A 1 N aqueous sulfuric acid solution (1 ml) was then added to the reaction solution, and the mixture was stirred at room temperature overnight. The reaction solution was made alkaline by the addition of 1 N sodium hydroxide, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with water and was dried over anhydrous sodium sulfate. The solvent was removed by distillation under the reduced pressure, and the residue was purified by thin layer chromatography using chloroform-methanol to give the title compound (29 mg, yield 45%).

후처리

  1. customto prepare a solution
  2. stirringthe mixture was stirred at room temperature overnight
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe ethyl acetate layer was washed with water
  5. dry with materialwas dried over anhydrous sodium sulfate
  6. customThe solvent was removed by distillation under the reduced pressure
  7. customthe residue was purified by thin layer chromatography

출처 및 근거

ORD 기록
ord-1e29acd55e944b2eaf02a3340412ba63
출처 데이터셋
uspto-grants-2009_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07560558B2

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