Vanillin → 4-Formyl-2-methoxyphenyl trifluoromethanesulfonate

HRID 1186976ノート

反応式

HRID 1186976 の反応式
[O:1]=[CH:2][C:3]1[CH:11]=[CH:10][C:8]([OH:9])=[C:5]([O:6][CH3:7])[CH:4]=1.C(=O)([O-])[O-].[K+].[K+].[F:18][C:19]([F:34])([F:33])[S:20](OC1C=CC([N+]([O-])=O)=CC=1)(=[O:22])=[O:21].CCOC(C)=O>CN(C=O)C>[F:18][C:19]([F:34])([F:33])[S:20]([O:9][C:8]1[CH:10]=[CH:11][C:3]([CH:2]=[O:1])=[CH:4][C:5]=1[O:6][CH3:7])(=[O:22])=[O:21]

参加物

6

反応物 4

HCID 1183VanillinHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 5498704-Nitrophenyl trifluoromethanesulfonate

生成物 1

HCID 108029624-Formyl-2-methoxyphenyl trifluoromethanesulfonate

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a solution of vanillin (20.0 g, 131 mmol) in DMF (200 mL) at room temperature was added potassium carbonate (36 g, 263 mmol) and 4-nitrophenyl trifluoromethanesulfonate (54.0 g, 197 mmol) and the reaction mixture was stirred for 8 h. EtOAc (600 mL) was added to the reaction mixture and the organic layer was washed three times with water, dried, filtered, and concentrated. The crude compound was then purified by flash chromatography (ethylacetate/hexanes 1:9→3:7) to provide 4-formyl-2-methoxyphenyl trifluoromethanesulfonate.

後処理

  1. washthe organic layer was washed three times with water
  2. customdried
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude compound was then purified by flash chromatography (ethylacetate/hexanes 1:9→3:7)

出典と根拠

ORDレコード
ord-99675710826f444084d85dfa532145c9
出典データセット
uspto-grants-2014_03
特許番号
US08673920B2

反応ノート

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