Acetonitrile → HCID 22504370, compound

HRID 1654127Notes

Reaction equation

HRID 1654127 reaction equation
Br[C:2]1[O:6][C:5]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[CH:4][CH:3]=1.C(#N)C.[C:15]([Si:17]([CH3:20])([CH3:19])[CH3:18])#[CH:16].P([O-])(O)(O)=O.[Na+]>[Cu](I)I.C(N(CC)CC)C>[CH3:18][Si:17]([C:15]#[C:16][C:2]1[O:6][C:5]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[CH:4][CH:3]=1)([CH3:20])[CH3:19]

Participants

7

Reactant 4

HCID 6342AcetonitrileHCID 66111TrimethylsilylacetyleneHCID 345282Ethyl 5-bromofuran-2-carboxylateHCID 23672064Monosodium phosphate

Product 1

HCID 22504370HCID 22504370, compound

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 8471TriethylamineSolvent

Procedure

A solution of 5 g of the product of Stage A, 15 ml of acetonitrile, 15 ml of triethylamine, 4.5 ml of ethynyltrimethylsilane, 170 mg of (triphenylphosphine)palladium chloride and 30 mg of copper iodide was heated at 40° C. for 2 and a half hours and then allowed to return to room temperature and was poured into an aqueous sodium dihydrogenphosphate solution. The mixture was extracted with ethyl acetate and the extract was washed with water and dried. The solvent was evaporated to obtain after chromatography on silica (eluent: 95/5 hexane/ethyl acetate) 4.75 g of the expected product.

Workup

  1. customto return to room temperature
  2. extractionThe mixture was extracted with ethyl acetate
  3. washthe extract was washed with water
  4. customdried
  5. customThe solvent was evaporated

Sources & evidence

ORD record
ord-9c9e74152e1d4572aa7f5f20a5e36702
Source dataset
uspto-grants-1995_04
Patent number
US05405865

Reaction notes

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