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HRID326931

反应详情

EQUATION

反应方程式

HRID 326931 的结构方程式

REACTANTS

反应物

3
结构：CC(=O)O
HCID176

Acetic Acid

C2H4O2

结构：COC(=O)c1ccccc1CC[C@H](O)c1cccc(C=Cc2ccc3ccc(Cl)cc3n2)c1
HCID54006303

Methyl 2-[(3S)-3-[3-[2-(7-chloro-2-quinolinyl)ethenyl]phenyl]-3-hydroxypropyl]benzoate

C28H24ClNO3

结构：C[Mg+].[Br-]
HCID178418689

未命名化合物

PRODUCTS

生成物

1
结构：CC(C)(O)c1ccccc1CC[C@H](O)c1cccc(C=Cc2ccc3ccc(Cl)cc3n2)c1
HCID54563620

(αS)-α-[3-[2-(7-Chloro-2-quinolinyl)ethenyl]phenyl]-2-(1-hydroxy-1-methylethyl)benzenepropanol

C29H28ClNO2

AUXILIARIES

试剂、催化剂与溶剂

2
结构：Cc1ccccc1
溶剂HCID1140

Toluene

C7H8

结构：C1CCOC1.Cc1ccccc1
溶剂HCID22635083

未命名化合物

PROCEDURE

实验过程

To a solution of the hydroxyester of Step 2 (38.68 g, 84.36 mmol) in 600 mL of toluene at 0° C. was added slowly 225 mL of 1.5M MeMgBr in toluene:THF 3:1 and the mixture was stirred at r.t. for 4 h. It was then poured into 2 L cold 12% NH4OAc and 25 mL of AcOH were added. The products were extracted in EtOAc, washed with brine, dried over Na2SO4 and concentrated. Flash chromatography of the residue with EtOAc:toluene 15:85 and 25:75 afforded first the methyl ketone derivative, then the title compound.

WORKUP

后处理

  1. additionwere added
  2. extractionThe products were extracted in EtOAc
  3. washwashed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customFlash chromatography of the residue with EtOAc:toluene 15:85 and 25:75 afforded first the methyl ketone derivative