Water → HCID 70128654, compound

HRID 1004340Notes

Reaction equation

HRID 1004340 reaction equation
[O:1]=[C:2]([C:17]([O:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:18])[CH:3]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH2:4][C:5]([O:7][C:8]([CH3:11])([CH3:10])[CH3:9])=[O:6].[H-].[Na+].[CH3:29][O:30][CH2:31]Cl.O>CN(C)C=O>[CH3:29][O:30][CH2:31][O:1][C:2]([C:17]([O:19][CH2:20][C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)=[O:18])=[C:3]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH2:4][C:5]([O:7][C:8]([CH3:9])([CH3:10])[CH3:11])=[O:6]

Participants

6

Reactant 4

HCID 962WaterHCID 7864Chloromethyl Methyl EtherHCID 24758Sodium hydrideHCID 70128516HCID 70128516, compound

Product 1

HCID 70128654HCID 70128654, compoundYield 86.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

992 mg of 1-benzyl 3-tert-butyl 2-ethyl 1-oxo-1,2,3-propanetricarboxylate in 10 ml of dimethylformamide was stirred together with 131 mg of 60% oily sodium hydride at room temperature for 1 hour. After addition of 273 mg of chloromethyl methyl ether, the reaction solution was stirred for another 45 minutes, then poured into water and extracted with ethyl ether. The organic layer was dried over anhydrous magnesium sulfate. The desiccant was filtered off, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography [hexane/ethyl acetate=5/1] to give 962 mg of the title compound as a colorless oily substance.

Workup

  1. extractionextracted with ethyl ether
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. filtrationThe desiccant was filtered off
  4. distillationthe solvent was distilled off under reduced pressure
  5. customThe residue was purified by silica gel column chromatography [hexane/ethyl acetate=5/1]

Sources & evidence

ORD record
ord-a644a88ec2a34367ae92256443a10656
Source dataset
uspto-grants-2000_04
Patent number
US06048894

Reaction notes

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