Methyl Acrylate → HCID 24799843, compound

HRID 1158538Notes

Reaction equation

HRID 1158538 reaction equation
[CH2:1]([C@@H:8]1[O:12][C:11]([CH3:14])([CH3:13])[O:10][C:9]1=[O:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Li+].CC([N-]C(C)C)C.[C:24]([O:28][CH3:29])(=[O:27])[CH:25]=[CH2:26]>C1COCC1>[CH3:29][O:28][C:24](=[O:27])[CH2:25][CH2:26][C:8]1([CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[C:9](=[O:15])[O:10][C:11]([CH3:13])([CH3:14])[O:12]1

Participants

5

Reactant 3

HCID 7294Methyl AcrylateHCID 2724682Lithium diisopropylamideHCID 10632081HCID 10632081, compound

Product 1

HCID 24799843HCID 24799843, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of compound 56 (3.180 g, 15.42 mmol) in THF was added 9.42 mL LDA (1.8 M in THF, 16.96 mmol) at −78° C. Methyl acrylate (1.460 g, 16.96 mmol) was added to the solution at −78° C. after 15 min. After 1 h the reaction was quenched with saturated NH4Cl aqueous solution, extracted with EtOAc 3×30 mL, dried with MgSO4 and purified on silica gel with 8-17% EtOAc-PE which gave the title compound (2.418 g, 54%) as colorless oil.

Workup

  1. customAfter 1 h the reaction was quenched with saturated NH4Cl aqueous solution
  2. extractionextracted with EtOAc 3×30 mL
  3. dry with materialdried with MgSO4
  4. custompurified on silica gel with 8-17% EtOAc-PE which

Sources & evidence

ORD record
ord-68f669e9fc9c484f87941fd26ca24eed
Source dataset
uspto-grants-2010_10
Patent number
US07807677B2

Reaction notes

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