Triphenylphosphine → HCID 10242213, compound

HRID 986892Notes

Reaction equation

HRID 986892 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:12]=[CH:13][CH:14]=1)[O:5]C1CCCOC1.[C:15]([C:17]1[CH:18]=[C:19]([CH:27]=[CH:28][CH:29]=1)[O:20]C1CCCOC1)#[CH:16].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(N(CC)CC)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>[OH:20][C:19]1[CH:18]=[C:17]([C:15]#[C:16][C:2]2[CH:14]=[CH:13][CH:12]=[C:4]([OH:5])[CH:3]=2)[CH:29]=[CH:28][CH:27]=1

Participants

7

Reactant 3

HCID 11776TriphenylphosphineHCID 22987400HCID 22987400, compoundHCID 22987406HCID 22987406, compound

Product 1

HCID 10242213HCID 10242213, compound

Reagents, catalysts & solvents 3

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

Procedure

Following the above procedure, the reaction was performed with 3-(3-bromophenoxy)tetrahydropyran (2.57 g), 3-(3 -ethynylphenoxy)tetrahydropyran (2.02 g), triphenylphosphine (105 mg), copper(I) iodide (19 mg) and bis(triphenylphosphine)palladium(II) dichloride (70 mg) in triethylamine (40 ml). The crude dark residue obtained after filtration over silica-gel column is dissolved in a mixture of dichloromethane (10 ml) and methanol (40 ml), then treated with 150 mg pyridinium p-toluene sulphonate at 60° C. for 2 h. The transparent reaction solution was then diluted with 100 ml of ether and washed twice with 40 ml of water then with 50 ml of saturated NaCl solution, dried over MgSO4 and evaporated to dryness to afford 1,2-bis-(3-hydroxyphenyl)ethyne as yellowish solid.

Workup

  1. customThe crude dark residue obtained
  2. filtrationafter filtration over silica-gel column
  3. dissolutionis dissolved in a mixture of dichloromethane (10 ml) and methanol (40 ml)
  4. additiontreated with 150 mg pyridinium p-toluene sulphonate at 60° C. for 2 h
  5. additionThe transparent reaction solution was then diluted with 100 ml of ether
  6. washwashed twice with 40 ml of water
  7. dry with materialwith 50 ml of saturated NaCl solution, dried over MgSO4
  8. customevaporated to dryness

Sources & evidence

ORD record
ord-a64ac2c7dbff4c33a1c876d4404c092f
Source dataset
uspto-grants-2003_10
Patent number
US06630076B1

Reaction notes

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