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

HRID 926757ノート

反応式

HRID 926757 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-2761cc4ab30643df8410c4f39e4fc870
出典データセット
uspto-grants-2016_03
特許番号
US09289429B2

反応ノート

読み込み中…