2-Methoxyethanol → HCID 58795642, compound

HRID 2390881Notes

Reaction equation

HRID 2390881 reaction equation
F[C:2](F)(F)[C:3]([NH:5][C:6]1[CH:16]=[CH:15][C:9]([C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:8][CH:7]=1)=O.[CH3:19][O:20]CCO.N(C(OC(C)C)=O)=NC(OC(C)C)=O>C1COCC1>[CH3:19][O:20][CH2:2][CH2:3][NH:5][C:6]1[CH:16]=[CH:15][C:9]([C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 80192-MethoxyethanolHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 261963ethyl 4-[(trifluoroacetyl)amino]benzoate

Product 1

HCID 58795642HCID 58795642, compoundYield 31.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 4-(2,2,2-trifluoro-acetylamino)-benzoate (1.58 g, 6.05 mmol, CASRN 24568-14-7) in dry THF was added 2-methoxyethanol (1.192 mL, 15.12 mmol), diisopropyl azodicarboxylate (2.94 mL, 15.12 mmol) and P (3.97 g, 15.12 mmol) and the resulting solution stirred for 4 h. The reaction mixture was concentrated, dissolved in EtOAc, washed sequentially with water and brine, dried (MgSO4), filtered and concentrated. The crude product was purified by SiO2 chromatography eluting with 50% EtOAc/hexane to afford 0.42 g of ethyl 4-(2-methoxy-ethylamino)-benzoate (338).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. dissolutiondissolved in EtOAc
  3. washwashed sequentially with water and brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude product was purified by SiO2 chromatography
  8. washeluting with 50% EtOAc/hexane

Sources & evidence

ORD record
ord-a6a6d80e07fb44bfbedd8e7271d90e14
Source dataset
uspto-grants-2012_09
Patent number
US08273773B2

Reaction notes

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