Sodium hydride → HCID 15837482, compound

HRID 1871279Notes

Reaction equation

HRID 1871279 reaction equation
[OH:1][CH:2]([C:7]([O:20][CH3:21])([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:3]([O:5][CH3:6])=[O:4].[H-].[Na+].Cl[C:25]1[CH:34]=[C:33]([CH3:35])[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[N:26]=1>CN(C)C=O>[CH3:35][C:33]1[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[N:26]=[C:25]([O:1][CH:2]([C:7]([O:20][CH3:21])([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:3]([O:5][CH3:6])=[O:4])[CH:34]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 694492-Chloro-4-methylquinolineHCID 10541193Methyl 2-hydroxy-3-methoxy-3,3-diphenylpropanoate

Product 1

HCID 15837482HCID 15837482, compoundYield 30.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5.7 g (20 mmol) of Methyl 2-hydroxy-3-methoxy-3,3-diphenyl-propionate were dissolved in 90 ml of dimethylformamide, and 0.98 g (22 mmol) of sodium hydride (55% in oil) was added. After stirring for 15 minutes, 3.9 g (22 mmol) of 2-chloro-4-methylquinoline were added. The dark red solution was stirred at room temperature overnight, then cautiously hydrolyzed with 20 ml of water and subsequently extracted with ethyl acetate. The organic phase was washed with water, and dried over magnesium sulfate, and the solvent was removed by distillation. The residue (8.1 g) was then chromatographed on silica gel, resulting in 2.6 g of impure product as oil.

Workup

  1. stirringThe dark red solution was stirred at room temperature overnight
  2. extractioncautiously hydrolyzed with 20 ml of water and subsequently extracted with ethyl acetate
  3. washThe organic phase was washed with water
  4. dry with materialdried over magnesium sulfate
  5. customthe solvent was removed by distillation
  6. customThe residue (8.1 g) was then chromatographed on silica gel

Sources & evidence

ORD record
ord-d1a53ec6b60347d5bd8a1d890f06beeb
Source dataset
uspto-grants-2000_08
Patent number
US06103732

Reaction notes

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