Triphenylphosphine → HCID 22987400, compound

HRID 986891Notes

Reaction equation

HRID 986891 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:12]=[CH:13][CH:14]=1)[O:5][CH:6]1[CH2:11][CH2:10][CH2:9][O:8][CH2:7]1.[C:15]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C[CH:16]=1.C[Si](C#C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C(N(CC)CC)C.C1COCC1.O.[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:15]([C:2]1[CH:3]=[C:4]([CH:12]=[CH:13][CH:14]=1)[O:5][CH:6]1[CH2:11][CH2:10][CH2:9][O:8][CH2:7]1)#[CH:16]

Participants

10

Reactant 4

HCID 11776TriphenylphosphineHCID 66111TrimethylsilylacetyleneHCID 2724141Tetrabutylammonium FluorideHCID 22987406HCID 22987406, compound

Product 1

HCID 22987400HCID 22987400, compound

Reagents, catalysts & solvents 5

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolvent

Conditions

Temperature
85 °C

Procedure

To a well degassed solution of 3-(3-bromophenoxy)tetrahydropyran (5.14 g), triphenylphosphine (204 mg), copper(I) iodide (38 mg) and bis(triphenylphosphine)palladium(II) dichloride (3.93 g) in triethylamine (40 ml), maintained under argon atmosphere, trimethylsilylacetylene is added and the mixture is stirred at 85° C. for 3 h. The precipitated ammonium salts was removed by filtration and the filtrate was evaporated to dryness. This affords a yellowish oil which is dissolved in 30 ml of THF containing 3 ml of water, then cooled at 0° C. and treated by dropwise addition of 5 ml of tetrabutylammonium fluoride (1M in THF). After stirring for 30 min the reaction was complete and the obtained brownish solution was filtered over a short silica-gel column and concentrated to yield a brownish residue, which was chromatographed on silica-gel column affording 3-(3-ethynylphenoxy)tetrahydropyran as yellowish crystals.

Workup

  1. customThe precipitated ammonium salts was removed by filtration
  2. customthe filtrate was evaporated to dryness
  3. customThis affords a yellowish oil which
  4. temperaturecooled at 0° C.
  5. stirringAfter stirring for 30 min the reaction
  6. filtrationthe obtained brownish solution was filtered over a short silica-gel column
  7. concentrationconcentrated
  8. customto yield a brownish residue, which
  9. customwas chromatographed on silica-gel column

Sources & evidence

ORD record
ord-7e98efa4991e49efa381ca068d9b01ca
Source dataset
uspto-grants-2003_10
Patent number
US06630076B1

Reaction notes

Loading…