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

HRID 409522

反応式

HRID 409522 の反応式
[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]

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 3776Isopropanol溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-cd93dc974e8f437fa39820e2702690eb
出典データセット
uspto-grants-2014_06
特許番号
US08759390B2

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