Ammonium Chloride → HCID 67365120, compound

HRID 217438Notes

Reaction equation

HRID 217438 reaction equation
Cl[C:2]([C:13]([F:16])([F:15])[F:14])=[C:3]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[C:4](=O)[CH3:5].C[S:18][CH2:19][C:20]([O-:22])=[O:21].[CH2:23]1CCN2C(=NCCC2)CC1.[NH4+].[Cl-]>CC#N>[CH3:5][C:4]1[C:3]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[C:2]([C:13]([F:16])([F:15])[F:14])[S:18][C:19]=1[C:20]([O:22][CH3:23])=[O:21]

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 5179950HCID 5179950, compoundHCID 72751052HCID 72751052, compound

Product 1

HCID 67365120HCID 67365120, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 4-chloro-5,5,5-trifluoro-3-phenylpent-3-en-2-one (950 mg) and methylsulfanylacetate (446 mg) in MeCN (23.8 mL) was added dropwise DBU (0.63 mL) at 25° C., followed by stirring at the same temperature for 15 hours. To the reaction liquid was added a saturated aqueous NH4Cl solution (50 mL), followed by extraction with diethylether (50 mL) three times. The organic layer was washed with brine, dried over MgSO4, and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (automatic purification device, hexane:EtOAc=98:2 to 90:0) to obtain methyl 3-methyl-4-phenyl-5-(trifluoromethyl)thiophene-2-carboxylate (1.08 g) as a colorless liquid.

Workup

  1. customTo the reaction liquid
  2. extractionfollowed by extraction with diethylether (50 mL) three times
  3. washThe organic layer was washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (automatic purification device, hexane:EtOAc=98:2 to 90:0)

Sources & evidence

ORD record
ord-666ff529af1e44bbb3a58508ab6692cc
Source dataset
uspto-grants-2012_06
Patent number
US08193378B2

Reaction notes

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