Trimethylsilylacetylene → HCID 86753785, compound

HRID 1417695Notes

Reaction equation

HRID 1417695 reaction equation
Br[C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH3:13])([CH3:12])[CH2:7][C:8]2=[O:11])=[CH:4][CH:3]=1.[CH3:14][Si:15]([C:18]#[CH:19])([CH3:17])[CH3:16]>CCN(CC)CC.[Cu]I.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl>[CH3:14][Si:15]([CH3:17])([CH3:16])[CH2:18][CH2:19][CH:7]1[C:6]([CH3:13])([CH3:12])[C:5]2[C:9](=[CH:10][CH:2]=[CH:3][CH:4]=2)[C:8]1=[O:11]

Participants

6

Reactant 2

HCID 66111TrimethylsilylacetyleneHCID 107763656-bromo-3,3-dimethyl-2,3-dihydro-1H-inden-1-one

Product 1

HCID 86753785HCID 86753785, compound

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalystHCID 8471TriethylamineSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 815.0 mg (3.41 mmol) 6-bromo-2,3-dihydro-3,3-dimethyl-1H-inden-1-one (See Smith et al. Org. Prep. Proced. Int. 1978 123-131) in 100 ml of degassed Et3N (sparged with argon for 20 min) was added 259.6 mg (1.363 mmol) of copper(I) iodide, 956.9 mg (1.363 mmol) of bis(triphenylphosphine)palladium(II)chloride, and 3.14 g (34.08 mmol) of (trimethylsilyl)acetylene. This mixture was heated at 70° C. for 42 hours, cooled to room temperature, and filtered through a pad of silica gel and washed with ether. The filtrate was washed with water, 1M HCl, water, and finally with saturated aqueous NaCl before being dried over MgSO4. Concentration of the solution under reduced pressure, followed by column chromatography (silica gel; 10% Et2O -hexanes) afforded the title compound as a brown oil. 1H NMR (300 MHz, CDCl3): δ 7.79(1H, d, J=1.4 Hz), 7.69 (1H, dd, J=1.6, 8.3 Hz), 7.42 (1H, d, J=8.5 Hz), 2.60 (2H, s), 1.41 (6H, s), 0.26 (9H, s).

Workup

  1. temperaturecooled to room temperature
  2. filtrationfiltered through a pad of silica gel
  3. washwashed with ether
  4. washThe filtrate was washed with water, 1M HCl, water
  5. dry with materialfinally with saturated aqueous NaCl before being dried over MgSO4

Sources & evidence

ORD record
ord-3efc821e7f924a21a17d00cd5c77c89c
Source dataset
uspto-grants-1999_03
Patent number
US05877207

Reaction notes

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