Sodium hydride → (3,3-Diphenylpropane-1-yl)4-methoxy-3-oxobutanoate

HRID 1297030Notes

Reaction equation

HRID 1297030 reaction equation
[C:1]1([CH:7]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:8][CH2:9][O:10][C:11](=[O:17])[CH2:12][C:13]([CH2:15]Cl)=[O:14])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].[CH3:26][O-:27].[Na+]>C1COCC1.CO>[C:1]1([CH:7]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:8][CH2:9][O:10][C:11](=[O:17])[CH2:12][C:13](=[O:14])[CH2:15][O:27][CH3:26])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 10942334Sodium MethoxideHCID 86760519(3,3-Diphenylpropane-1-yl)4-chloroacetoacetate

Product 1

HCID 70119313(3,3-Diphenylpropane-1-yl)4-methoxy-3-oxobutanoate

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 8028TetrahydrofuranSolvent2×

Procedure

2.5 ml of a solution of 0.879 mg (2.66 mmol) of (3,3-diphenylpropane-1-yl)4-chloroacetoacetate in 2.5 ml of THF was added dropwise to a suspension of 160 mg of sodium hydride (60% oily) in 5 ml of THF at 0° C. and they were stirred for 30 minutes. 820 μl of 28% solution of sodium methoxide in methanol was added to the obtained mixture. After stirring overnight, methanol was added to the reaction mixture, and the obtained mixture was concentrated and fractionated with ethyl acetate and water. After the drying over sodium sulfate followed by the purification by the silica gel chromatography (hexane/ethyl acetate=3/1), the title compound was obtained.

Workup

  1. stirringAfter stirring overnight
  2. concentrationthe obtained mixture was concentrated
  3. customAfter the drying over sodium sulfate followed by the purification by the silica gel chromatography (hexane/ethyl acetate=3/1)

Sources & evidence

ORD record
ord-075edbbaf07f4da2ab76854596bba7fd
Source dataset
uspto-grants-2007_07
Patent number
US07247645B2

Reaction notes

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