Water → {4-[2-(2-Chloro-6-methoxy-phenyl)-2-hydroxy-ethyl]-3-nitro-phenyl}-carbamic acid tert-butyl ester

HRID 1051225ノート

反応式

HRID 1051225 の反応式
[C:1]([O:5][C:6](=[O:22])[NH:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][Si](C)(C)C)=[C:10]([N+:19]([O-:21])=[O:20])[CH:9]=1)([CH3:4])([CH3:3])[CH3:2].[Cl:23][C:24]1[CH:31]=[CH:30][CH:29]=[C:28]([O:32][CH3:33])[C:25]=1[CH:26]=[O:27].[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O>C1COCC1>[C:1]([O:5][C:6](=[O:22])[NH:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][CH:26]([C:25]2[C:28]([O:32][CH3:33])=[CH:29][CH:30]=[CH:31][C:24]=2[Cl:23])[OH:27])=[C:10]([N+:19]([O-:21])=[O:20])[CH:9]=1)([CH3:4])([CH3:3])[CH3:2]

参加物

6

反応物 4

HCID 962WaterHCID 2724141Tetrabutylammonium FluorideHCID 109649712-Chloro-6-methoxybenzaldehydeHCID 90102892HCID 90102892、化合物

生成物 1

HCID 90103009{4-[2-(2-Chloro-6-methoxy-phenyl)-2-hydroxy-ethyl]-3-nitro-phenyl}-carbamic acid tert-butyl ester収率 35%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
25 °C

実験手順

A solution of (3-nitro-4-trimethylsilanylmethyl-phenyl)-carbamic acid tert-butyl ester (1.00 g, 3.08 mmol) and 2-chloro-6-methoxybenzaldehyde (526 mg, 3.08 mmol) in THF (10 mL) was added tetra-butylammonium fluoride (121 mg, 462 μmol) at 25° C., the color of the solution changed to dark blue after the addition. The reaction mixture was stirred at 25° C. for 30 min and poured into water. The aqueous phase was extracted three times with ethyl acetate. The combined organic layers were washed with brine and dried over magnesium sulfate. Filtration followed by concentration in vacuo gave a brown solid. Flash chromatography (70/30 hexanes/ethyl acetate) afforded {4-[2-(2-chloro-6-methoxy-phenyl)-2-hydroxy-ethyl]-3-nitro-phenyl}-carbamic acid tert-butyl ester (0.45 g, 35%) as an oil.

後処理

  1. additionafter the addition
  2. extractionThe aqueous phase was extracted three times with ethyl acetate
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationFiltration
  6. concentrationfollowed by concentration in vacuo
  7. customgave a brown solid

出典と根拠

ORDレコード
ord-08224acda1144e04b13f781ee1117470
出典データセット
uspto-grants-2016_07
特許番号
US09388166B2

反応ノート

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