Vanillin → 2-Phenoxyacetamide

HRID 1820006ノート

反応式

HRID 1820006 の反応式
O[C:2]1[CH:9]=[CH:8][C:5](C=O)=[CH:4][C:3]=1[O:10][CH3:11].BrC[C:14]([NH:16]C1C=CC(Br)=CC=1)=[O:15].C(=O)([O-])[O-].[K+].[K+].C(#N)CC>C(OCC)(=O)C>[O:10]([CH2:11][C:14]([NH2:16])=[O:15])[C:3]1[CH:2]=[CH:9][CH:8]=[CH:5][CH:4]=1

参加物

6

反応物 4

HCID 1183VanillinHCID 7854PropionitrileHCID 11430Potassium CarbonateHCID 2255262-Bromo-n-(4-bromophenyl)acetamide

生成物 1

HCID 693142-Phenoxyacetamide収率 190%

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

反応条件

温度
80 °C

実験手順

To 4-hydroxy-3-methoxybenzaldehyde (2.02 g, 13.3 mmol), 2-bromo-N-(4-bromophenyl)acetamide (3.00 g, 10.2 mmol) and potassium carbonate (2.12 g, 15.4 mmol) was added propionitrile (10 ml), and the mixture was stirred at 80° C. for one day. The reaction mixture was diluted with ethyl acetate, washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the obtained residue was purified by alumina column chromatography (developing solvent; ethyl acetate), and powderized with ethyl acetate-diisopropyl ether (1:5) to give a phenoxyacetamide derivative (2.93 g). The title compound was obtained by similar operations as in Reference Example 43 and Example 6 and using this compound.

後処理

  1. washwashed with saturated brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. customThe solvent was evaporated under reduced pressure
  4. customthe obtained residue was purified by alumina column chromatography (developing solvent; ethyl acetate)

出典と根拠

ORDレコード
ord-a87d2fb6c4d143778be2bab68757a9a6
出典データセット
uspto-grants-2009_10
特許番号
US07601868B2

反応ノート

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