Trimethylsilylacetylene → HCID 21846695, compound

HRID 619612Notes

Reaction equation

HRID 619612 reaction equation
FC(F)(F)S(O[C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][C:16]=1[F:17])[S:13][C:12]([CH3:19])([CH3:18])[CH2:11][C:10]2=[O:20])(=O)=O.[CH3:23][Si:24]([C:27]#[CH:28])([CH3:26])[CH3:25]>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>[CH3:18][C:12]1([CH3:19])[CH2:11][C:10](=[O:20])[C:9]2[C:14](=[CH:15][C:16]([F:17])=[C:7]([C:28]#[C:27][Si:24]([CH3:26])([CH3:25])[CH3:23])[CH:8]=2)[S:13]1

Participants

7

Reactant 2

HCID 66111TrimethylsilylacetyleneHCID 21846685HCID 21846685, compound2×

Product 1

HCID 21846695HCID 21846695, compoundYield 78%

Reagents, catalysts & solvents 4

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

Conditions

Temperature
95 °C

Procedure

A solution of 2,2-dimethyl-4-oxo-7-fluoro-thiochroman-6-yl trifluoromethanesulfonate (Compound 205, 1.28 g, 3.57 mmol) in 6.0 mL Et3N and 15.0 mL DMF was sparged with argon for 15 minutes. To this solution was added trimethylsilylacetylene (2.0 g, 20.4 mmol) and bis(triphenylphosphine)-palladium(II) chloride (100.0 mg, 0.14 mmol). The solution was heated to 95° C. for 6 hours, cooled to room temperature and stirred overnight. The solution was diluted with H2O and extracted with EtOAc. The combined organic layers were washed with H2O, saturated aqueous NaCl and dried over MgSO4. Concentration of the dry solution under reduced pressure and isolation of the product by column chromatography (3 to 5% EtOAc/hexanes) afforded 850.0 mg (78%) of the title compound as an orange solid. 1H NMR (300 MHz, CDCl3)δ: 8.22 (1H, d, J=7.5 Hz), 6.92 (1H, d, J=9.3 Hz), 2.85 (2H, s), 1.46 (6H, s), 0.25 (9H, S).

Workup

  1. temperaturecooled to room temperature
  2. extractionextracted with EtOAc
  3. washThe combined organic layers were washed with H2O, saturated aqueous NaCl
  4. dry with materialdried over MgSO4

Sources & evidence

ORD record
ord-6409cbe6b1474f23b7ccf19f9ea4a14c
Source dataset
uspto-grants-1999_09
Patent number
US05958954

Reaction notes

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