Trimethylsilylacetylene → HCID 21957873, compound

HRID 2213552Notes

Reaction equation

HRID 2213552 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]>C(N(CC)CC)C.CN(C)C=O.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])[CH2:11][C:10](=[O:19])[C:9]2[C:14](=[CH:15][CH:16]=[C:7]([C:27]#[C:26][Si:23]([CH3:25])([CH3:24])[CH3:22])[CH:8]=2)[S:13]1

Participants

7

Reactant 2

HCID 66111TrimethylsilylacetyleneHCID 10286711HCID 10286711, compound

Product 1

HCID 21957873HCID 21957873, 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-oxothiochroman-6-yl trifluoromethanesulfonate (2.88 g, 8.50 mmol) in 10 mL triethylamine (Et3N) and 20.0 mL dimethylformamide (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 hours, 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 the 2,2-dimethyl-6-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, 8.1 Hz), 7.15 (1H, d, J=8.1 Hz), 2.85 (2H, s), 1.45 (6H, s), 0.23 (9H, s).

Workup

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

Sources & evidence

ORD record
ord-fa23133c038d468cb701516367262f4e
Source dataset
uspto-grants-2006_09
Patent number
US07105566B2

Reaction notes

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