Ethyl Acetate → methyl 2-nitro-3-(tetrahydro-2H-pyran-4-yloxy)benzoate

HRID 1672461Notes

Reaction equation

HRID 1672461 reaction equation
[OH:1][C:2]1[C:3]([N+:12]([O-:14])=[O:13])=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].CS(O[CH:20]1[CH2:25][CH2:24][O:23][CH2:22][CH2:21]1)(=O)=O.C([O-])([O-])=O.[K+].[K+].C(OCC)(=O)C>CC#N>[N+:12]([C:3]1[C:2]([O:1][CH:20]2[CH2:25][CH2:24][O:23][CH2:22][CH2:21]2)=[CH:11][CH:10]=[CH:9][C:4]=1[C:5]([O:7][CH3:8])=[O:6])([O-:14])=[O:13]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 11344352Oxan-4-yl methanesulfonateHCID 13659833Methyl 3-hydroxy-2-nitrobenzoate

Product 1

HCID 58082227methyl 2-nitro-3-(tetrahydro-2H-pyran-4-yloxy)benzoateYield 136.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Methyl 3-hydroxy-2-nitrobenzoate (95 g, 0.52 mol), tetrahydro-2H-pyran-4-yl methanesulfonate (234 g, 1.3 mol) and K2CO3 (358 g, 2.6 mol) was suspend in MeCN (2 L). The mixture was heated at reflux for 20 h. TLC (petroleum ether:ethyl acetate=1:1) showed the reaction was complete. The mixture was filtered; the filtrate was concentrated in vacuo. The residue was purified by chromatography (petroleum ether: ethyl acetate=10:1, 5:1, 2:1) to give the title compound (200 g 100%) as a yellow oil.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 20 h
  3. filtrationThe mixture was filtered
  4. concentrationthe filtrate was concentrated in vacuo
  5. customThe residue was purified by chromatography (petroleum ether: ethyl acetate=10:1, 5:1, 2:1)

Sources & evidence

ORD record
ord-b87ec786704d44489d96f70a14df63bf
Source dataset
uspto-grants-2011_08
Patent number
US07998978B2

Reaction notes

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