Formaldehyde → 6-hydroxy-7-(morpholinomethyl)benzofuran-3(2H)-one

HRID 1749792Notes

Reaction equation

HRID 1749792 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[CH:3]=1.[NH:12]1[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1.[CH2:18]=O>C(O)C>[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[CH2:18][N:12]1[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 8083MorpholineHCID 2357176-Hydroxy-3-coumaranone

Product 1

HCID 712789376-hydroxy-7-(morpholinomethyl)benzofuran-3(2H)-oneYield 40%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 6-hydroxybenzofuran-3(2H)-one (1.50 g, 10.0 mmol) in ethanol (10 mL) was added with morpholine (0.871 g, 10.0 mmol), and 37% aqueous formaldehyde (0.812 g, 10.0 mmol) at room temperature. The mixture was stirred overnight at room temperature, and then the filtrate was concentrated. The resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate) to obtain the objective 6-hydroxy-7-(morpholinomethyl)benzofuran-3(2H)-one (0.987 g, 40%).

Workup

  1. concentrationthe filtrate was concentrated
  2. customThe resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-9c879659dc6a4e2e9ecc7a32f76d3f82
Source dataset
uspto-grants-2015_10
Patent number
US09156827B2

Reaction notes

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