Vanillin → 4-Formyl-2-methoxyphenyl trifluoromethanesulfonate

HRID 1186976노트

반응식

HRID 1186976 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

HCID 108029624-Formyl-2-methoxyphenyl trifluoromethanesulfonate

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-99675710826f444084d85dfa532145c9
출처 데이터셋
uspto-grants-2014_03
특허 번호
US08673920B2

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