Methyl Thioglycolate → HCID 22149005, compound

HRID 441162Notes

Reaction equation

HRID 441162 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:16][C:11]3[C:12](=[O:15])[O:13][CH2:14][C:10]=3[C:9]=2[C:17]2[CH:22]=[CH:21][C:20]([S:23](C)(=[O:25])=[O:24])=[CH:19][CH:18]=2)=[CH:4][CH:3]=1.C(OC)(=O)CS.C1CCN2C(=[N:37]CCC2)CC1>CC#N>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:16][C:11]3[C:12](=[O:15])[O:13][CH2:14][C:10]=3[C:9]=2[C:17]2[CH:22]=[CH:21][C:20]([S:23]([NH2:37])(=[O:25])=[O:24])=[CH:19][CH:18]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 16907Methyl ThioglycolateHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 22148988HCID 22148988, compound

Product 1

HCID 22149005HCID 22149005, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of cis,trans-4-chloro-4-(4-fluorophenyl)-3-(4-(methylthio)phenyl)-3-buten-2-one (13.8 g) (Example 6, Step 3) and methyl thioglycolate (5.8 mL) in 350 mL of CH3CN was added 8 mL of DBU. After stirring for 5 h, the reaction was quenched with 250 mL of sat. NH4Cl and 50 mL of 1N HCl. The mixture was then extracted with 800 ml of 2:1 EtOAc/hexane. The extract was dried over MgSO4 and concentrated in vacuo. The residue was purified by flash chromatography eluted with 10:1 hexane/EtOAc to provide 8.58 g of the title compound.

Workup

  1. customthe reaction was quenched with 250 mL of sat. NH4Cl and 50 mL of 1N HCl
  2. extractionThe mixture was then extracted with 800 ml of 2:1 EtOAc/hexane
  3. dry with materialThe extract was dried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by flash chromatography
  6. washeluted with 10:1 hexane/EtOAc

Sources & evidence

ORD record
ord-70f49fc8a5f34ef78ed6c006cd7202f4
Source dataset
uspto-grants-1996_05
Patent number
US05521213

Reaction notes

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