Water → Methyl 4-chloro-3-nitro-5-[2-(tetrahydro-pyran-2-yloxy)-ethoxy]-benzoate

HRID 368741Notes

Reaction equation

HRID 368741 reaction equation
[Cl:1][C:2]1[C:11]([N+:12]([O-:14])=[O:13])=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[OH:15].C(=O)([O-])[O-].[K+].[K+].I[CH2:23][CH2:24][O:25][CH:26]1[CH2:31][CH2:30][CH2:29][CH2:28][O:27]1.O>CC(C)=O>[Cl:1][C:2]1[C:3]([O:15][CH2:23][CH2:24][O:25][CH:26]2[CH2:31][CH2:30][CH2:29][CH2:28][O:27]2)=[CH:4][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:10][C:11]=1[N+:12]([O-:14])=[O:13]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 111186622H-Pyran, tetrahydro-2-(2-iodoethoxy)-HCID 23288674HCID 23288674, compound

Product 1

HCID 23288648Methyl 4-chloro-3-nitro-5-[2-(tetrahydro-pyran-2-yloxy)-ethoxy]-benzoate

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

6.84 g of methyl 4-chloro-3-hydroxy-5-nitro-benzoate were dissolved in acetone (150 ml), treated at RT in succession with 10.19 g of potassium carbonate and 11.19 g of 2-(2-iodo-ethoxy)-tetrahydro-pyran and the mixture was heated at reflux for 16 hours. Subsequently, the mixture was poured into water, extracted with ethyl acetate, the organic phase was dried over sodium sulphate and concentrated on a rotary evaporator. The residue was flash chromatographed on silica gel with hexane/ether (2/1) as the eluent. There was thus obtained the desired methyl 4-chloro-3-nitro-5-[2-(tetrahydro-pyran-2-yloxy)-ethoxy]-benzoate as as a pale yellow solid.

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 16 hours
  3. extractionextracted with ethyl acetate
  4. dry with materialthe organic phase was dried over sodium sulphate
  5. concentrationconcentrated on a rotary evaporator
  6. customchromatographed on silica gel with hexane/ether (2/1) as the eluent

Sources & evidence

ORD record
ord-6cac0c8c87d34376976bcd48d1171f67
Source dataset
uspto-grants-2000_10
Patent number
US06133442

Reaction notes

Loading…