Sodium hydride → HCID 66921638, compound

HRID 1362842Notes

Reaction equation

HRID 1362842 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5](=[O:12])[CH:6]([CH3:11])[C:7]([O:9][CH3:10])=[O:8].Cl[CH2:14][O:15][C:16]1[CH:21]=[CH:20][C:19]([O:22][CH2:23][CH3:24])=[CH:18][CH:17]=1.[Cl-].[NH4+]>O1CCCC1.O>[CH3:3][O:4][C:5](=[O:12])[C:6]([CH2:14][O:15][C:16]1[CH:21]=[CH:20][C:19]([O:22][CH2:23][CH3:24])=[CH:18][CH:17]=1)([CH3:11])[C:7]([O:9][CH3:10])=[O:8]

Participants

7

Reactant 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 69104Dimethyl methylmalonateHCID 22961214HCID 22961214, compound

Product 1

HCID 66921638HCID 66921638, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

11.5 g of sodium hydride (55% in oil) are suspended in 150 ml of tetrahydrofurane under nitrogen atmosphere. 29.6 g of methyl-malonic acid dimethyl ester are added during 20 minutes while maintaining the temperature at +25° C. by cooling. Stirring is continued until the gas evolution ceased. 37.8 g of 1-Chlormethoxy-4-ethoxy-benzene are then added over a period of 20 minutes maintaining the temperature at around +30° C. After 1.5 hours the mixture is cooled to +5° C. and 25 ml of ammonium chloride is added carefully, then poured into water and extracted with ethyl acetate. The organic phase is washed with brine and dried over sodium sulfate, filtered and the solvent evaporated. Flash chromatography (eluant: hexane/ethyl acetate 95:5) yielded 41.6 g of a slightly yellow powder.

Workup

  1. temperaturewhile maintaining the temperature at +25° C.
  2. temperatureby cooling
  3. temperaturemaintaining the temperature at around +30° C
  4. temperatureAfter 1.5 hours the mixture is cooled to +5° C.
  5. extractionextracted with ethyl acetate
  6. washThe organic phase is washed with brine
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. customthe solvent evaporated
  10. customFlash chromatography (eluant: hexane/ethyl acetate 95:5) yielded 41.6 g of a slightly yellow powder

Sources & evidence

ORD record
ord-df81165a2bdc43ad9a61df4579d291f6
Source dataset
uspto-grants-2011_02
Patent number
US07884103B2

Reaction notes

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