Methanol → Methyl 3-(4-(methylthio)phenyl)propanoate

HRID 1099668

반응식

HRID 1099668 반응식
[CH3:1][S:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][C:11]([OH:13])=[O:12])=[CH:5][CH:4]=1.[CH:14]1N=CN(C(N2C=NC=C2)=O)C=1.CO>CN(C=O)C>[CH3:1][S:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:9][CH2:10][C:11]([O:13][CH3:14])=[O:12])=[CH:7][CH:8]=1

참가 물질

5

반응물 3

HCID 887MethanolHCID 682631,1'-CarbonyldiimidazoleHCID 38010983-[4-(Methylsulfanyl)phenyl]propanoic acid

생성물 1

HCID 21914741Methyl 3-(4-(methylthio)phenyl)propanoate수율 72%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

In a 100 mL round bottom flask, 3-(4-(methylthio)phenyl)propanoic acid (1.00 g, 5.10 mmol) was dissolved in DMF (17 mL) under N2(g). CDI (1.24 g, 7.65 mmol) was then added to the reaction mixture and the resulting mixture was allowed to stir at room temperature for ˜45 min. MeOH (6 μL) was then added in dropwise fashion to the reaction. The reaction was allowed to stir for an additional 1 h, after which time it was extracted with EtOAc (3×50 μL) and brine (3×50 mL). The combined organic extracts were dried over anhydrous Na2SO4(s), filtered and concentrated. The crude product was purified by column chromatography (silica gel, gradient elution mixture: 10% EtOAc in Hexanes to 100% EtOAc) to give the title compound (0.771 g, 72%).

후처리

  1. stirringto stir for an additional 1 h
  2. extractionafter which time it was extracted with EtOAc (3×50 μL) and brine (3×50 mL)
  3. dry with materialThe combined organic extracts were dried over anhydrous Na2SO4(s)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude product was purified by column chromatography (silica gel, gradient elution mixture: 10% EtOAc in Hexanes to 100% EtOAc)

출처 및 근거

ORD 기록
ord-3d0daa4d4e114bfd9cfd046c2bd76794
출처 데이터셋
uspto-grants-2012_03
특허 번호
US08143410B2

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