Methanol → 3-(2-Acetylphenyl)-1(R)-(3-(2-(7-chloro-2-quinolinyl)ethenyl)phenyl)propanol

HRID 249042노트

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HRID 249042 반응식
C[Mg+].[Br-].[C:4]1(C)C=CC=CC=1.C1COCC1.[Cl:16][C:17]1[CH:26]=[C:25]2[C:20]([CH:21]=[CH:22][C:23]([CH:27]=[CH:28][C:29]3[CH:30]=[C:31]([C@H:35]([OH:48])[CH2:36][CH2:37][C:38]4[CH:47]=[CH:46][CH:45]=[CH:44][C:39]=4[C:40]([O:42]C)=O)[CH:32]=[CH:33][CH:34]=3)=[N:24]2)=[CH:19][CH:18]=1.CO>C1COCC1.O>[C:40]([C:39]1[CH:44]=[CH:45][CH:46]=[CH:47][C:38]=1[CH2:37][CH2:36][C@H:35]([C:31]1[CH:32]=[CH:33][CH:34]=[C:29]([CH:28]=[CH:27][C:23]2[CH:22]=[CH:21][C:20]3[C:25](=[CH:26][C:17]([Cl:16])=[CH:18][CH:19]=3)[N:24]=2)[CH:30]=1)[OH:48])(=[O:42])[CH3:4]

참가 물질

7

반응물 4

HCID 887MethanolHCID 22635083Tetrahydrofuran tolueneHCID 54006302Methyl 2-(3-(3-(2-(7-chloro-2-quinolinyl)ethenyl)phenyl)-3(R)-hydroxypropyl)benzoateHCID 178418689HCID 178418689, 화합물

생성물 1

HCID 541389713-(2-Acetylphenyl)-1(R)-(3-(2-(7-chloro-2-quinolinyl)ethenyl)phenyl)propanol

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

At 0° C., a 1.5M MeMgBr solution in toluene:THF 1:1 (130 mL, 195 mmol) was added dropwise to a solution of the hydroxyester of Step 3 (11.04 g, 24.1 mmol) (dried in EtOAc and stripped with toluene to remove the H2O) and MeOH (2.0 mL, 49.4 mmol) in 240 mL of anhydrous THF. The reaction mixture was stirred at r.t. for 2.5 h and was then poured into ice cold 25% NH4OAc. The product was extracted into EtOAc, dried over Na2SO4 and purified by flash chromatography on silica with EtOAc:toluene 10:90 and 15:85. [α]D : +23.8° (c=1.04, CHCl3).

후처리

  1. dry with materialdried in EtOAc
  2. extractionThe product was extracted into EtOAc
  3. dry with materialdried over Na2SO4
  4. custompurified by flash chromatography on silica with EtOAc:toluene 10:90 and 15:85
  5. custom+23.8° (c=1.04, CHCl3)

출처 및 근거

ORD 기록
ord-bb244d466d1d4fe38f0e0028a18486db
출처 데이터셋
uspto-grants-1993_05
특허 번호
US05212180

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