Methyl Acrylate → 3-((3-Methoxy-3-oxopropylthio)methyl)benzoic acid

HRID 926757노트

반응식

HRID 926757 반응식
[SH:1][CH2:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[C:6]([OH:8])=[O:7].[C:12]([O:16][CH3:17])(=[O:15])[CH:13]=[CH2:14].N12CCCN=C1CCCCC2>C(#N)C>[CH3:17][O:16][C:12](=[O:15])[CH2:13][CH2:14][S:1][CH2:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[C:6]([OH:8])=[O:7]

참가 물질

5

반응물 3

HCID 7294Methyl AcrylateHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 113211893-(mercaptomethyl)benzoic acid

생성물 1

HCID 434082543-((3-Methoxy-3-oxopropylthio)methyl)benzoic acid

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

Into a 50-mL round bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed a solution of 3-(mercaptomethyl)benzoic acid (500 mg, 2.97 mmol, 1.00 equiv) in acetonitrile (10.0 mL), then methyl acrylate (10.0 mL) and 1,8-diazabicyclo[5.4.0]undec-7-ene (1.0 g, 6.57 mmol, 2.00 equiv) were added in series. The resulting solution was heated to reflux overnight. The resulting mixture was concentrated under vacuum. The residue was applied onto a silica gel column and eluted with ethyl acetate/petroleum ether (0˜1:6). This resulted in 220 mg (28%) of 3-((3-methoxy-3-oxopropylthio)methyl)benzoic acid as a light-red oil.

후처리

  1. customInto a 50-mL round bottom flask purged
  2. temperaturemaintained with an inert atmosphere of nitrogen
  3. temperatureThe resulting solution was heated
  4. temperatureto reflux overnight
  5. concentrationThe resulting mixture was concentrated under vacuum
  6. washeluted with ethyl acetate/petroleum ether (0˜1:6)
  7. customThis resulted in 220 mg (28%) of 3-((3-methoxy-3-oxopropylthio)methyl)benzoic acid as a light-red oil

출처 및 근거

ORD 기록
ord-2761cc4ab30643df8410c4f39e4fc870
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09289429B2

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