Methyl Acrylate → HCID 58573085, compound

HRID 931950Notes

Reaction equation

HRID 931950 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9]([C:11]2[S:12][C:13]([Cl:16])=[CH:14][CH:15]=2)=[O:10])[CH:5]=[CH:6][CH:7]=1.[CH3:17][O:18][C:19](=[O:22])[CH:20]=[CH2:21].N12CCCN=C1CCCCC2>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]([C:9]([C:11]2[S:12][C:13]([Cl:16])=[CH:14][CH:15]=2)=[O:10])[CH2:21][CH2:20][C:19]([O:18][CH3:17])=[O:22])[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 7294Methyl AcrylateHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 58573959HCID 58573959, compound

Product 1

HCID 58573085HCID 58573085, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To a solution of 7.35 g (27.1 mmol) of 2-(3-chlorophenyl)-1-(5-chlorothiophen-2-yl)ethanone (Example 63, Step A) and acrylic acid methyl ester (2.81 mL, 31.2 mmol) in DCM (60 mL) was added 1,8-diazabicyclo[5.4.0]undec-7-ene (4.05 mL, 27.1 mmol) in DCM (10 mL) slowly at 0° C. over 20 min. Then the reaction was allowed to warm to ambient temperature. After being stirred at 25° C. for two days, the reaction mixture was diluted with DCM and washed with 2N HCl, water and sat. aq. NaCl solution. The organic extract was dried over Na2SO4. The solution was filtered and concentrated in vacuo to give the crude material as light yellow oil. The crude material was absorbed onto a plug of silica gel and purified by chromatography through a pre-packed silica gel column (220 g), eluting with a gradient of 0% to 30% EtOAc in hexane, to provided the title compound as a light-yellow oil.

Workup

  1. washwashed with 2N HCl, water and sat. aq. NaCl solution
  2. extractionThe organic extract
  3. dry with materialwas dried over Na2SO4
  4. filtrationThe solution was filtered
  5. concentrationconcentrated in vacuo
  6. customto give the crude material as light yellow oil
  7. customThe crude material was absorbed onto a plug of silica gel
  8. custompurified by chromatography through a pre-packed silica gel column (220 g)
  9. washeluting with a gradient of 0% to 30% EtOAc in hexane

Sources & evidence

ORD record
ord-c9629553c5504a32a2b33ed383f760af
Source dataset
uspto-grants-2016_03
Patent number
US09296736B2

Reaction notes

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