(Trifluoromethyl)trimethylsilane → HCID 71075240, compound

HRID 1851962Notes

Reaction equation

HRID 1851962 reaction equation
[F:1][C:2]([Si](C)(C)C)([F:4])[F:3].[CH:9]([C:12]1[CH:13]=[C:14]([CH:23]=[CH:24][CH:25]=1)/[CH:15]=[N:16]/[S@:17]([C:19]([CH3:22])([CH3:21])[CH3:20])=[O:18])([CH3:11])[CH3:10]>C1COCC1>[CH3:22][C:19]([S@@:17]([NH:16][C@H:15]([C:14]1[CH:23]=[CH:24][CH:25]=[C:12]([CH:9]([CH3:11])[CH3:10])[CH:13]=1)[C:2]([F:4])([F:3])[F:1])=[O:18])([CH3:20])[CH3:21]

Participants

4

Reactant 2

HCID 552549(Trifluoromethyl)trimethylsilaneHCID 89252079HCID 89252079, compound

Product 1

HCID 71075240HCID 71075240, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Tetra-n-butylammonium difluorotriphenylsilicate (TBAT) (1.19 g, 2.13 mmol) and (trifluoromethyl)trimethylsilane (TMS-CF3) (0.371 mL, 2.33 mmol) was added to a solution of (S,E)-N-(3-isopropylbenzylidene)-2-methylpropane-2-sulfinamide (0.487 g, 1.937 mmol) in anhydrous THF (16 mL) at −20° C. under argon. The reaction was allowed to proceed for ˜2 h where the starting material appeared to have been consumed as determined by analytical-HPLC. A saturated solution of NH4Cl (20 mL) was added to quench and the mixture was extracted with EtOAc (100 mL×3) and dried over Na2 SO4. The organic partition was then concentrated to an oil and the title compound was isolated by flash chromatography using silica gel (EtOAc:Hexanes). ESI-MS (m/z): 321 [M+1]+.

Workup

  1. customto have been consumed
  2. additionA saturated solution of NH4Cl (20 mL) was added
  3. customto quench
  4. extractionthe mixture was extracted with EtOAc (100 mL×3)
  5. customdried over Na2 SO4
  6. customThe organic partition
  7. concentrationwas then concentrated to an oil

Sources & evidence

ORD record
ord-7cd993321c8e4415a302942dba0b94aa
Source dataset
uspto-grants-2015_02
Patent number
US08957093B2

Reaction notes

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