(Diethylamino)sulfur trifluoride → HCID 67537887, compound

HRID 2241015Notes

Reaction equation

HRID 2241015 reaction equation
[F:1][CH:2]([F:24])[O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10](=[O:23])[C:11]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([C:19]#[C:20][CH2:21]O)[CH:14]=2)=[O:12])=[CH:6][CH:5]=1.CCN(S(F)(F)[F:31])CC.C([O-])(O)=O.[Na+]>C(Cl)Cl>[F:1][CH:2]([F:24])[O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10](=[O:23])[C:11]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([C:19]#[C:20][CH2:21][F:31])[CH:14]=2)=[O:12])=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 123472(Diethylamino)sulfur trifluorideHCID 516892Sodium BicarbonateHCID 67539293HCID 67539293, compound

Product 1

HCID 67537887HCID 67537887, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

1-(4-(Difluoromethoxy)phenyl)-2-(3-(3-hydroxyprop-1-ynyl)phenyl)ethane-1,2-dione (0.298 g, 0.90 mmol) is dissolved in CH2Cl2 (3.0 mL) and cooled to −78° C. DAST (0.160 g, 0.99 mmol) is added and the solution is slowly warmed to RT. After 1 h at RT a saturated solution of NaHCO3 is added and the mixture extracted with CH2Cl2. The CH2Cl2 is washed with H2O and brine. The solution is dried (MgSO4) and the material purified by flash chromatography to yield 1-(4-(difluoromethoxy)phenyl)-2-(3-(3-fluoroprop-1-ynyl)phenyl)ethane-1,2-dione (0.232, 77%).

Workup

  1. temperaturethe solution is slowly warmed to RT
  2. extractionthe mixture extracted with CH2Cl2
  3. washThe CH2Cl2 is washed with H2O and brine
  4. dry with materialThe solution is dried (MgSO4)
  5. customthe material purified by flash chromatography

Sources & evidence

ORD record
ord-2986bc0e26eb4722a644e1824c3df81a
Source dataset
uspto-grants-2010_05
Patent number
US07723368B2

Reaction notes

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