Triphenylphosphine → 2-(4-Phenylbut-1-ynyl)benzo[d]oxazole

HRID 334532Notes

Reaction equation

HRID 334532 reaction equation
Cl[C:2]1[O:3][C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH2:30]([C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[CH2:31][C:32]#[CH:33]>C(N(CC)CC)C.CN(C=O)C.[Cu]I.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>[C:34]1([CH2:30][CH2:31][C:32]#[C:33][C:2]2[O:3][C:4]3[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=3[N:6]=2)[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1

Participants

8

Reactant 3

HCID 11776TriphenylphosphineHCID 119862-ChlorobenzoxazoleHCID 1233604-Phenyl-1-butyne

Product 1

HCID 115650272-(4-Phenylbut-1-ynyl)benzo[d]oxazoleYield 40.5%

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of CuI (15 mg, 81 mmol) in triethylamine (3 mL) were added 2-chlorobenzo[d]oxazole (250 mg, 1.63 mmol), (PPh3)2PdCl2 (57 mg, 81 μmol), triphenylphosphine polymer bound 3 mmol/g (98 mg, 293 μmol) and a solution of 1-(but-3-ynyl)benzene (250 mg, 1.92 mmol) in DMF (0.5 mL). The reaction mixture was stirred for 25 min. at 120° C. in the microwave cavity. The reaction was quenched as described in Example 1. The crude residue was purified by flash chromatography (cyclohexane/AcOEt 95:5) to yield 163 mg (0.66 mmol, 40%) of 2-(4-phenylbut-1-ynyl)benzo[d]oxazole as an orange oil.

Workup

  1. customThe reaction was quenched
  2. customThe crude residue was purified by flash chromatography (cyclohexane/AcOEt 95:5)

Sources & evidence

ORD record
ord-0cda3b02d8404878ba77c92541c44658
Source dataset
uspto-grants-2014_11
Patent number
US08883826B2

Reaction notes

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