Methanol → 6-methoxy-7-(morpholinomethyl)benzofuran-3(2H)-one

HRID 1749896Notes

Reaction equation

HRID 1749896 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][C:5]2[C:6](=[O:9])[CH2:7][O:8][C:4]=2[C:3]=1[CH2:12][N:13]1[CH2:18][CH2:17][O:16][CH2:15][CH2:14]1.CO.[C:21]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O.C1(C)C=CC=CC=1>C1COCC1>[CH3:21][O:1][C:2]1[CH:11]=[CH:10][C:5]2[C:6](=[O:9])[CH2:7][O:8][C:4]=2[C:3]=1[CH2:12][N:13]1[CH2:18][CH2:17][O:16][CH2:15][CH2:14]1

Participants

7

Reactant 5

HCID 887MethanolHCID 1140TolueneHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 712789376-hydroxy-7-(morpholinomethyl)benzofuran-3(2H)-one

Product 1

HCID 712789876-methoxy-7-(morpholinomethyl)benzofuran-3(2H)-oneYield 82.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 6-hydroxy-7-(morpholinomethyl)benzofuran-3(2H)-one (0.586 g, 2.35 mmol), methanol (0.0904 g, 2.82 mmol) and triphenylphosphine (0.923 g, 3.52 mmol) in THF (12 mL) was added with a solution of a 40% solution of diethyl azodicarboxylate in toluene (1.84 g, 4.23 mmol) in THF (6 mL), and the mixture was stirred overnight at room temperature. The reaction mixture was concentrated, and the resulting residue was purified by silica gel column chromatography (chloroform/methanol) to obtain 6-methoxy-7-(morpholinomethyl)benzofuran-3(2H)-one (0.509 g, 82%).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe resulting residue was purified by silica gel column chromatography (chloroform/methanol)

Sources & evidence

ORD record
ord-a1e233f9bff44d329b2c3eb8daa4f6d4
Source dataset
uspto-grants-2015_10
Patent number
US09156827B2

Reaction notes

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