Acetic Acid → Racemic tert-butyl 2-(3,4-dichlorophenyl)-6-methoxy-4-oxochroman-3-carboxylate

HRID 409522

Reaktionsgleichung

Reaktionsgleichung von HRID 409522
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[C:10](=[O:19])[CH2:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13].[Cl:20][C:21]1[CH:22]=[C:23]([CH:26]=[CH:27][C:28]=1[Cl:29])[CH:24]=O.N1CCCCC1.C(O)(=O)C>C(O)(C)C.O>[Cl:20][C:21]1[CH:22]=[C:23]([CH:24]2[CH:11]([C:12]([O:14][C:15]([CH3:16])([CH3:18])[CH3:17])=[O:13])[C:10](=[O:19])[C:3]3[C:2](=[CH:7][CH:6]=[C:5]([O:8][CH3:9])[CH:4]=3)[O:1]2)[CH:26]=[CH:27][C:28]=1[Cl:29]

Komponenten

7

Edukt 4

HCID 176Acetic AcidHCID 8082PiperidineHCID 227103,4-DichlorobenzaldehydeHCID 67155884Tert-butyl 3-(2-hydroxy-5-methoxyphenyl)-3-oxopropanoate

Produkt 1

HCID 67156193Racemic tert-butyl 2-(3,4-dichlorophenyl)-6-methoxy-4-oxochroman-3-carboxylateAusbeute 48 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 3776IsopropanolLösungsmittel

Versuchsvorschrift

A solution of tert-butyl 3-(2-hydroxy-5-methoxyphenyl)-3-oxopropanoate (500 mg, 1.88 mmol) in isopropanol (5.0 mL) was treated with 3,4-dichlorobenzaldehyde (329 mg, 1.88 mmol), piperidine (20 μL, 188 μmol) and acetic acid (10 μL, 188 μmol). The reaction mixture was heated at reflux overnight, and then treated with water (1.0 mL). The resulting mixture was cooled to rt and then concentrated under vacuum to yield a residue. The residue was purified by column chromatography (silica gel, 2-25% ethyl acetate-hexane) to provide racemic tert-butyl 2-(3,4-dichlorophenyl)-6-methoxy-4-oxochroman-3-carboxylate as a yellow oil (380 mg, 48%). This material was used without further purification in Step 3 below.

Aufarbeitung

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux overnight
  3. concentrationconcentrated under vacuum
  4. customto yield a residue
  5. customThe residue was purified by column chromatography (silica gel, 2-25% ethyl acetate-hexane)

Quellen und Nachweise

ORD-Eintrag
ord-cd93dc974e8f437fa39820e2702690eb
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08759390B2

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