Formaldehyde → HCID 60155785, compound

HRID 1749830Notes

Reaction equation

HRID 1749830 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.[N:12]1([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:18][CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1.[CH2:26]=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[CH2:26][N:15]1[CH2:16][CH2:17][CH2:18][N:12]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:13][CH2:14]1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 2357176-Hydroxy-3-coumaranoneHCID 2756058Tert-butyl 1,4-diazepane-1-carboxylate

Product 1

HCID 60155785HCID 60155785, compoundYield 16.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 6-hydroxybenzofuran-3(2H)-one (0.150 g, 1.00 mmol) in ethanol (1 mL) was added with tert-butyl 1,4-diazepane-1-carboxylate (0.200 g, 1.00 mmol) and paraformaldehyde (0.0300 g, 1.00 mmol) at room temperature, and the mixture was refluxed for 3 hours by heating. The reaction mixture was concentrated, and the resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate) to obtain tert-butyl 4-[(6-hydroxy-3-oxo-2,3-dihydrobenzofuran-7-yl)methyl]-1,4-diazepane-1-carboxylate (0.0583 g, 16%).

Workup

  1. temperaturethe mixture was refluxed for 3 hours
  2. temperatureby heating
  3. concentrationThe reaction mixture was concentrated
  4. customthe resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-e5f982689a8a404b823ec3eb9c400950
Source dataset
uspto-grants-2015_10
Patent number
US09156827B2

Reaction notes

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