2-Methoxyethanol → HCID 23024267, compound

HRID 915913Notes

Reaction equation

HRID 915913 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]([OH:12])[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH3:32][O:33][CH2:34][CH2:35]O.N(C(OCC)=O)=NC(OCC)=O>C(OCC)(=O)C.O1CCCC1>[OH:1][C:2]1[CH:11]=[C:10]([O:12][CH2:35][CH2:34][O:33][CH3:32])[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5]

Participants

7

Reactant 4

HCID 80192-MethoxyethanolHCID 11776TriphenylphosphineHCID 16523Methyl 2,4-DihydroxybenzoateHCID 220568ethyl N-ethoxycarbonyliminocarbamate

Product 1

HCID 23024267HCID 23024267, compoundYield 87.5%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a 50 ml tetrahydrofuran solution of 4.0 g (23.8 mmol) of methyl 2,4-dihydroxybenzoate, 7.49 g (28.5 mmol) of triphenylphosphine, 2.25 ml (28.5 mmol) of 2-methoxyethanol, and 4.5 ml (28.5 mmol) of diethyl azodicarboxylate were slowly added at 0° C. The mixture was brought to room temperature, and stirred for 1 hour. Then, the reaction mixture was diluted with ethyl acetate, and washed with water and a saturated aqueous solution of sodium chloride. The washed system was dried over sodium sulfate, and then the solvent was distilled off under reduced pressure. To the residue, 100 ml of a solution of ethyl acetate/hexane (=1/4) was added, and insoluble solids were removed by filtration. Then, the mother liquor was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (hexane/ethyl acetate=6/1) to obtain 4.71 g (87%) of the captioned compound.

Workup

  1. customwas brought to room temperature
  2. washwashed with water
  3. dry with materialThe washed system was dried over sodium sulfate
  4. distillationthe solvent was distilled off under reduced pressure
  5. additionTo the residue, 100 ml of a solution of ethyl acetate/hexane (=1/4) was added
  6. custominsoluble solids were removed by filtration
  7. concentrationThen, the mother liquor was concentrated under reduced pressure
  8. customthe residue was purified by silica gel column chromatography (hexane/ethyl acetate=6/1)

Sources & evidence

ORD record
ord-0e9ead3cf54a4b758161de3ff070449a
Source dataset
uspto-grants-2007_09
Patent number
US07268128B2

Reaction notes

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