Water → HCID 22504370, compound

HRID 1432268Notes

Reaction equation

HRID 1432268 reaction equation
Br[C:2]1[O:3][C:4]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[CH:5][CH:6]=1.C(N(CC)CC)C.O.[CH3:20][Si:21]([C:24]#[CH:25])([CH3:23])[CH3:22]>CN(C)C=O>[CH2:10]([O:9][C:7]([C:4]1[O:3][C:2]([C:25]#[C:24][Si:21]([CH3:23])([CH3:22])[CH3:20])=[CH:6][CH:5]=1)=[O:8])[CH3:11]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 66111TrimethylsilylacetyleneHCID 345282Ethyl 5-bromofuran-2-carboxylate

Product 1

HCID 22504370HCID 22504370, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of the compound obtained in Example 29 (1) (0.5 g) in N,N-dimethylformamide (5 ml), trimethylsilylacetylene (0.65 ml), bistriphenylphosphine palladium dichloride (0.16 g), cuprous iodide (0.04 g) and triethylamine (0.64 ml) were added successively and the mixture was stirred in a sealed tube at 100° C. for 2 hours. After cooling, the reaction solution was poured into water, extracted with ethyl acetate, washed with a saturated aqueous NaCl solution, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The resulting residue was separated using silica gel column chromatography (hexane:ethyl acetate=4:1) to obtain 0.3782 g of the desired product as a brown oil.

Workup

  1. temperatureAfter cooling
  2. extractionextracted with ethyl acetate
  3. washwashed with a saturated aqueous NaCl solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe resulting residue was separated

Sources & evidence

ORD record
ord-1a5a78e0ca3b4d75be18f549b2d8feb1
Source dataset
uspto-grants-2009_11
Patent number
US07612070B2

Reaction notes

Loading…