Methyl 4-acetylbenzoate → HCID 57925876, compound

HRID 1013476Notes

Reaction equation

HRID 1013476 reaction equation
[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:9]=[CH:8][C:7]([C:10](=[O:12])[CH3:11])=[CH:6][CH:5]=1.[P:14]([O-:19])([O:17][CH3:18])[O:15][CH3:16]>C1COCC1.CCOC(C)=O>[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:9]=[CH:8][C:7]([C:10]([P:14]([O:17][CH3:18])([O:15][CH3:16])=[O:19])([OH:12])[CH3:11])=[CH:6][CH:5]=1

Participants

5

Reactant 2

HCID 137990Methyl 4-acetylbenzoateHCID 21884954Dimethylphosphite

Product 1

HCID 57925876HCID 57925876, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 4-acetyl-benzoic acid methyl ester (1.0 g, 5.61 mmol) in THF (5.6 mL) was cooled to 0° C. and dimethyl phosphite (0.7 g, 6.17 mmol) and N,N,N′N′-tetramethyl-guanidine (0.07 g, 0.56 mmol) were added dropwise. The reaction mixture was warmed to ambient temperature and stirred for 30 minutes. The reaction mixture was diluted with EtOAc and washed with 1N aqueous HCl (2×), brine, then dried (MgSO4) and concentrated in vacuo. The residue was purified by MPLC (Isocratic CH2Cl2 for 6 CV then 0-7.5% MeOH in CH2Cl2) to afford the title compound: MS: cal'd 289 (MH+), exp 289 (MH+)

Workup

  1. washwashed with 1N aqueous HCl (2×), brine
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by MPLC (Isocratic CH2Cl2 for 6 CV

Sources & evidence

ORD record
ord-f0d6d8654e22415bbb89319f9e01e952
Source dataset
uspto-grants-2011_07
Patent number
US07981874B2

Reaction notes

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