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

HRID 409522

반응식

HRID 409522 반응식
[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]

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 3776Isopropanol용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-cd93dc974e8f437fa39820e2702690eb
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08759390B2

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