Phenol → HCID 89581070, compound

HRID 1501249Notes

Reaction equation

HRID 1501249 reaction equation
[OH:1][CH:2]([C:4]1[N:9]=[N:8][C:7]([C:10]([O:12][CH3:13])=[O:11])=[CH:6][CH:5]=1)[CH3:3].[C:14]1(O)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>O1CCCC1>[O:1]([CH:2]([C:4]1[N:9]=[N:8][C:7]([C:10]([O:12][CH3:13])=[O:11])=[CH:6][CH:5]=1)[CH3:3])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 996PhenolHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 89581124HCID 89581124, compound

Product 1

HCID 89581070HCID 89581070, compoundYield 70.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 6-(1-hydroxyethyl)pyridazine-3-carboxylate (100 mg, 0.55 mmol), phenol (78 mg, 0.8 mmol), triphenylphosphine (216 mg, 0.8 mmol) in tetrahydrofuran (30 mL) was added diisopropyl azodicarboxylate (166 mg, 0.8 mmol) at room temperature. The mixture solution was stirred for 18 hours. Then tetrahydrofuran was removed in vacuo. The residue was purified by column chromatography (silica-gel, petroleum/ethyl acetate=5:1) to give methyl 6-(1-phenoxyethyl)pyridazine-3-carboxylate as a colorless oil (100 mg, 70%). 1H NMR (300 MHz, DMSO-d6): δ 8.20 (d, J=9 Hz, 1H), 7.93 (d, J=9 Hz, 1H), 7.20-7.25 (m, 2H), 6.87-6.94 (m, 3H), 5.87-5.90 (m, 1H), 3.94 (s, 3H), 1.68 (d, J=6 Hz, 3H).

Workup

  1. customThen tetrahydrofuran was removed in vacuo
  2. customThe residue was purified by column chromatography (silica-gel, petroleum/ethyl acetate=5:1)

Sources & evidence

ORD record
ord-19302c84576e41d0a92a7e4908be6b80
Source dataset
uspto-grants-2015_12
Patent number
US09206128B2

Reaction notes

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