Diethylene Glycol Monomethyl Ether → HCID 58506478, compound

HRID 2167303Notes

Reaction equation

HRID 2167303 reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([OH:8])[CH:5]=[CH:4][C:3]=1[N:9]1[CH:13]=[CH:12][C:11]([C:14]([O:16][CH3:17])=[O:15])=[N:10]1.[CH3:18][O:19][CH2:20][CH2:21][O:22][CH2:23][CH2:24]O.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[OH:1][C:2]1[CH:7]=[C:6]([O:8][CH2:24][CH2:23][O:22][CH2:21][CH2:20][O:19][CH3:18])[CH:5]=[CH:4][C:3]=1[N:9]1[CH:13]=[CH:12][C:11]([C:14]([O:16][CH3:17])=[O:15])=[N:10]1

Participants

6

Reactant 4

HCID 8134Diethylene Glycol Monomethyl EtherHCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 58506493HCID 58506493, compound

Product 1

HCID 58506478HCID 58506478, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 1-(2,4-dihydroxyphenyl)-1H-pyrazole-3-carboxylate 3 (200 mg, 0.855 mmol, 1.00 equiv) in THF (5 mL), 2-(2-methoxyethoxy)ethanol (103 mg, 0.855 mmol, 1.00 equiv) was added Ph3P (223 mg, 0.855 mmol, 1.00 equiv), and DEAD (149 mg, 0.855 mmol, 1.00 equiv) at 0° C. The resulting solution was stirred overnight. The solvent was concentrated under vacuum, the residue was applied onto a silica gel column and eluted with PE/EA (1/1). This resulted in 70 mg (50%) of methyl 1-(2-hydroxy-4-(2-(2-methoxyethoxy)ethoxy)phenyl)-1H-pyrazole-3-carboxylate 4 as a green oil.

Workup

  1. concentrationThe solvent was concentrated under vacuum
  2. washeluted with PE/EA (1/1)
  3. customThis resulted in 70 mg (50%) of methyl 1-(2-hydroxy-4-(2-(2-methoxyethoxy)ethoxy)phenyl)-1H-pyrazole-3-carboxylate 4 as a green oil

Sources & evidence

ORD record
ord-cee943ff848c473dbe55276f2942fa19
Source dataset
uspto-grants-2015_06
Patent number
US09045440B2

Reaction notes

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