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p-METHYLACETOPHENONE → 1-[4-(2-Methylquinolin-4-ylmethoxy)benzenesulfonyl]-2-p-tolylpropan-2-ol

HRID 1788370
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HRID 1788370 반응식
[CH3:1][S:2]([C:5]1[CH:23]=[CH:22][C:8]([O:9][CH2:10][C:11]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[N:14]=[C:13]([CH3:21])[CH:12]=2)=[CH:7][CH:6]=1)(=[O:4])=[O:3].C([N-]C(C)C)(C)C.[Li+].[CH3:32][C:33]1[CH:38]=[CH:37][C:36]([C:39](=[O:41])[CH3:40])=[CH:35][CH:34]=1>O1CCCC1.[Cl-].[Na+].O>[CH3:21][C:13]1[CH:12]=[C:11]([CH2:10][O:9][C:8]2[CH:7]=[CH:6][C:5]([S:2]([CH2:1][C:39]([C:36]3[CH:37]=[CH:38][C:33]([CH3:32])=[CH:34][CH:35]=3)([OH:41])[CH3:40])(=[O:4])=[O:3])=[CH:23][CH:22]=2)[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[N:14]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 3

HCID 8500p-METHYLACETOPHENONEHCID 2724682Lithium diisopropylamideHCID 230180214-(4-Methanesulfonylphenoxymethyl)-2-methylquinoline

생성물 1

HCID 230179531-[4-(2-Methylquinolin-4-ylmethoxy)benzenesulfonyl]-2-p-tolylpropan-2-ol수율 66%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매2회
HCID 57417360
Sodium chloride; water
용매

실험 절차

Under an atmosphere of argon, a solution of 473 mg (1.44 mmol) of 4-(4-methanesulfonylphenoxymethyl)-2-methylquinoline in tetrahydrofuran was cooled to −78° C. and then, 1.44 mL (1.44 mmol) of 2 M lithium diisopropylamide was added thereto and stirred for 40 minutes. Into this solution was dropped a solution of 194 mg (1.59 mmol) of p-methylacetophenone in tetrahydrofuran, followed by stirring for 2.5 hours. The reaction was stopped by the addition of saturated brine, extracted with ethyl acetate, dried over anhydrous magnesium sulfate, and filtered, and the filtrate was concentrated under a reduced pressure. The obtained residue was purified by column chromatography on silica gel (developing solvent; hexane:ethyl acetate=1:1 to 1:2) to obtain 440 mg (0.95 mmol) of 1-[4-(2-methylquinolin-4-ylmethoxy)benzenesulfonyl]-2-p-tolylpropan-2-ol (VIII-57). Its physical property is shown below.

후처리

  1. stirringby stirring for 2.5 hours
  2. extractionextracted with ethyl acetate
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated under a reduced pressure
  6. customThe obtained residue was purified by column chromatography on silica gel (developing solvent; hexane:ethyl acetate=1:1 to 1:2)

출처 및 근거

ORD 기록
ord-97adc6632ffe4899b931aa4034848e5d
출처 데이터셋
uspto-grants-2009_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07511144B2

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