Water → Ethyl 3-(3-((dimethylamino)methyl)-4-hydroxyphenyl)-2-methylpropanoate

HRID 1876404

반응식

HRID 1876404 반응식
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH:9]([CH3:15])[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[CH3:23][N+:24](=[CH2:26])[CH3:25].O>C1(C)C=CC=CC=1>[CH3:23][N:24]([CH2:26][C:7]1[CH:6]=[C:5]([CH2:8][CH:9]([CH3:15])[C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH:4]=[CH:3][C:2]=1[OH:1])[CH3:25]

참가 물질

6

반응물 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 2724133Dimethyl(methylene)ammounium iodideHCID 20748401Ethyl 3-(4-hydroxyphenyl)-2-methylpropanoate

생성물 1

HCID 58566359Ethyl 3-(3-((dimethylamino)methyl)-4-hydroxyphenyl)-2-methylpropanoate

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

To a solution of ethyl 3-(4-hydroxyphenyl)-2-methylpropanoate (672) (150 mg, 0.72 mmol), potassium carbonate (149.3 mg, 1.08 mmol) in toluene (7 mL) was added N,N-dimethylmethylideneammonium iodide (173.2 mg, 0.94 mmol) and stirred for 72 hours. Water was added and the reaction was extracted with ethyl acetate and the combined organic layers dried over sodium sulfate, filtered and concentrated in vacuo. The crude compound was purified by flash column chromatography on silica gel with hexanes and EtOAc (50%) to give ethyl 3-(3-((dimethylamino)methyl)-4-hydroxyphenyl)-2-methylpropanoate (673).

후처리

  1. extractionthe reaction was extracted with ethyl acetate
  2. dry with materialthe combined organic layers dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe crude compound was purified by flash column chromatography on silica gel with hexanes and EtOAc (50%)

출처 및 근거

ORD 기록
ord-eac68235966345758a0c07d7003749e2
출처 데이터셋
uspto-grants-2012_11
특허 번호
US08309600B2

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