Trimethylsilylacetylene → HCID 22323749, compound

HRID 324251Notes

Reaction equation

HRID 324251 reaction equation
FC(F)(F)S(O[C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[S:13][C:12]([CH3:18])([CH3:17])[CH2:11][C:10]2=[O:19])(=O)=O.[CH3:22][Si:23]([C:26]#[CH:27])([CH3:25])[CH3:24]>CCN(CC)CC.CN(C=O)C.O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:17][C:12]1([CH3:18])[CH:11]([C:27]#[C:26][Si:23]([CH3:25])([CH3:24])[CH3:22])[C:10](=[O:19])[C:9]2[C:14](=[CH:15][CH:16]=[CH:7][CH:8]=2)[S:13]1

Participants

7

Reactant 2

HCID 66111TrimethylsilylacetyleneHCID 10286711HCID 10286711, compound

Product 1

HCID 22323749HCID 22323749, compoundYield 91%

Reagents, catalysts & solvents 4

HCID 178418476HCID 178418476, compoundCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Conditions

Temperature
95 °C

Procedure

A solution of 2,2-dimethyl-4-oxo-thiochroman-6-yl trifluoromethanesulfonate (2.88 g. 8.50 mmol) in 10 mL Et3N and 20.0 mL DMF was sparged with argon for 10 minutes. To this solution was added trimethylsilylacetylene (4.15 g. 42.0 mmol) and bis(triphenylphosphine)-palladium(II) chloride (298.0 mg. 0.425 mmol). The solution was heated to 95° C. for 5 h, cooled to room temperature, and diluted with H2O. Extraction with EtOAc was followed by washing the combined organic layers, with H2O and saturated aqueous NaCl and drying over MgSO4. Concentration of the dry solution under reduced pressure and isolation of the product by column chromatography (3% EtOAc/hexanes) afforded 2.23 g (91%) of 2,2-dimethyl-trimethylsilanylethynyl-thiochroman-4-one as an orange oil. 1H NMR (300 MHz, CDCl3) δ: 8.18 (1H, d, J=1.9 Hz), 7.34 (1H, dd, J=1.9, 8.2 Hz), 7.15 (1H, d, J=8.1 Hz), 2.85 (2H, s), 1.45 (6H, s), 0.23 (9H0, s).

Workup

  1. temperaturecooled to room temperature
  2. extractionExtraction with EtOAc
  3. washby washing the combined organic layers
  4. dry with materialwith H2O and saturated aqueous NaCl and drying over MgSO4

Sources & evidence

ORD record
ord-3ebeec32c3c74f6d8c7ccc3870125ab7
Source dataset
uspto-grants-2001_04
Patent number
US06218128B1

Reaction notes

Loading…