Formaldehyde → HCID 71278800, compound

HRID 1749925Notes

Reaction equation

HRID 1749925 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.[CH3:12][S:13]([N:16]1[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]1)(=[O:15])=[O:14].[CH2:22]=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[CH2:22][N:19]1[CH2:20][CH2:21][N:16]([S:13]([CH3:12])(=[O:15])=[O:14])[CH2:17][CH2:18]1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 2357176-Hydroxy-3-coumaranoneHCID 7091611-(Methylsulfonyl)piperazine

Product 1

HCID 71278800HCID 71278800, compoundYield 12.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 6-hydroxybenzofuran-3(2H)-one (0.600 g, 4.00 mmol) in ethanol (4 mL) was added with 1-(methylsulfonyl)piperazine (0.657 g, 4.00 mmol), and 37% aqueous formaldehyde (0.325 g, 4.00 mmol) at room temperature. The reaction mixture was stirred overnight at room temperature, and then concentrated. The resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate) to obtain 6-hydroxy-7-{[4-(methylsulfonyl)piperazin-1-yl]methyl}benzofuran-3(2H)-one (0.169 g, 12%).

Workup

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

Sources & evidence

ORD record
ord-11ddbdc696f147078b490653667f6536
Source dataset
uspto-grants-2015_10
Patent number
US09156827B2

Reaction notes

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