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

HRID 249042Notes

Reaction equation

HRID 249042 reaction equation
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]

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-bb244d466d1d4fe38f0e0028a18486db
Source dataset
uspto-grants-1993_05
Patent number
US05212180

Reaction notes

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