Formaldehyde → Tert-butyl 4-[(6-hydroxy-3-oxo-2,3-dihydrobenzofuran-7-yl)methyl]piperazine-1-carboxylate

HRID 1749728Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1749728
[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.[C:12]([O:16][C:17]([N:19]1[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]1)=[O:18])([CH3:15])([CH3:14])[CH3:13].[CH2:25]=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[CH2:25][N:22]1[CH2:23][CH2:24][N:19]([C:17]([O:16][C:12]([CH3:15])([CH3:13])[CH3:14])=[O:18])[CH2:20][CH2:21]1

Komponenten

5

Edukt 3

HCID 712FormaldehydeHCID 143452tert-Butyl piperazine-1-carboxylateHCID 2357176-Hydroxy-3-coumaranone

Produkt 1

HCID 60155786Tert-butyl 4-[(6-hydroxy-3-oxo-2,3-dihydrobenzofuran-7-yl)methyl]piperazine-1-carboxylateAusbeute 50,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A solution of 6-hydroxybenzofuran-3(2H)-one (3.00 g, 20.0 mmol) in ethanol (20 mL) was added with 1-tert-butoxycarbonylpiperazine (3.73 g, 20.0 mmol), and 37% aqueous formaldehyde (1.62 g, 20.0 mmol) at room temperature. The mixture was stirred overnight at room temperature, and then subjected to suction filtration, and the filtrate was concentrated. Crude product obtained by silica gel column chromatography (hexane/ethyl acetate) was recrystallized from ethyl acetate to obtain the objective tert-butyl 4-[(6-hydroxy-3-oxo-2,3-dihydrobenzofuran-7-yl)methyl]piperazine-1-carboxylate (3.51 g, 50%).

Aufarbeitung

  1. filtrationsubjected to suction filtration
  2. concentrationthe filtrate was concentrated
  3. customCrude product obtained by silica gel column chromatography (hexane/ethyl acetate)
  4. customwas recrystallized from ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-d47d30ce2e7148ee8811470a4664c4e1
Quelldatensatz
uspto-grants-2015_10
Patentnummer
US09156827B2

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