Hydrochloric Acid → HCID 70673606, compound

HRID 341331Notes

Reaction equation

HRID 341331 reaction equation
[CH3:1][Si:2]([CH3:16])([CH3:15])[CH:3]=[CH:4][C:5]([O:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:6].CN(C)C(N(C)C)=N.Cl.[N+:26]([CH3:29])([O-:28])=[O:27]>>[N+:26]([CH2:29][CH:3]([Si:2]([CH3:15])([CH3:1])[CH3:16])[CH2:4][C:5]([O:7][CH2:8][C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1)=[O:6])([O-:28])=[O:27]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 6375NitromethaneHCID 664601,1,3,3-TetramethylguanidineHCID 86709898HCID 86709898, compound

Product 1

HCID 70673606HCID 70673606, compoundYield 88%

Procedure

A solution of benzyl 3-(trimethylsilyl)acrylate (782 mg, 3.34 mmol) in nitromethane (3 ml)was added with N,N,N′,N′-tetramethylguanidine (105 μl, 0.838 mmol) at room temperature, and the mixture was stirred for 15 hours. The reaction mixture was added with aqueous hydrochloric acid (1 N), and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium hydrogencarbonate and water, and dried over anhydrous sodium sulfate, and the solvent was evaporated. The residue was purified by silica gel chromatography [hexane/ethyl acetate (14:1)] to obtain benzyl 4-nitro-3-(trimethylsilyl)butanoate (863 mg, 88%) mentioned in the title as colorless oil.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated aqueous sodium hydrogencarbonate and water
  3. dry with materialdried over anhydrous sodium sulfate
  4. customthe solvent was evaporated
  5. customThe residue was purified by silica gel chromatography [hexane/ethyl acetate (14:1)]

Sources & evidence

ORD record
ord-4c7ca60e07f74c8790f8d99f2d07ae4e
Source dataset
uspto-grants-2014_11
Patent number
US08895769B2

Reaction notes

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