Triphenylphosphine → HCID 18383984, compound

HRID 2297732Notes

Reaction equation

HRID 2297732 reaction equation
[CH:1]#[C:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].I[C:10]1[CH:11]=[C:12]([CH:15]=[CH:16][C:17]=1[O:18][CH2:19][O:20][CH3:21])[CH:13]=[O:14].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(Cl)Cl.[Cu](I)I.C([O-])(=O)C.C([O-])(=O)C.[Pd+2]>[C:1]([C:10]1[CH:11]=[C:12]([CH:15]=[CH:16][C:17]=1[O:18][CH2:19][O:20][CH3:21])[CH:13]=[O:14])#[C:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

7

Reactant 3

HCID 11776TriphenylphosphineHCID 123701-OctyneHCID 10402059Benzaldehyde, 3-iodo-4-(methoxymethoxy)-

Product 1

HCID 18383984HCID 18383984, compoundYield 45.2%

Reagents, catalysts & solvents 3

HCID 83717Copper iodideCatalystHCID 167845palladium(II) acetateCatalystHCID 6344DichloromethaneSolvent

Procedure

Under an argon atmosphere, copper iodide (190 mg, 1.0 mmol), 1-octyne (0.55 mL, 5.0 mmol) and 3-iodo-4-methoxymethoxybenzaldehyde (291 mg, 1.0 mmol) were added to a solution (2 mL) of palladium (II) diacetate (11 mg, 0.05 mmol) and triphenylphosphine (52 mg, 0.20 mmol) in methylene chloride, followed by stirring at room temperature for 2 hours. Next, the reaction solution was filtered through celite, and the solvent contained in the filtrate was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (eluted with ethyl acetate/hexane=1/10) to give 3-(1-octyn-1-yl)-4-methoxymethoxybenzaldehyde (124 mg, yield 45%).

Workup

  1. filtrationNext, the reaction solution was filtered through celite
  2. customwas evaporated under reduced pressure
  3. customThe residue was purified by silica gel column chromatography (eluted with ethyl acetate/hexane=1/10)

Sources & evidence

ORD record
ord-b2f9cf1afa254210951bad91ae577cd5
Source dataset
uspto-grants-2002_12
Patent number
US06492392B1

Reaction notes

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