Propargyl alcohol → HCID 59407550, compound

HRID 1093453Notes

Reaction equation

HRID 1093453 reaction equation
[F:1][C:2]1[C:7]([F:8])=[C:6]([F:9])[CH:5]=[CH:4][C:3]=1I.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH2:30]([OH:33])[C:31]#[CH:32].C(N(C(C)C)CC)(C)C>[Cl-].[Na+].O.[Cu]I.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C(Cl)(Cl)Cl.[Pd].[Pd].O1CCCC1>[F:1][C:2]1[C:7]([F:8])=[C:6]([F:9])[CH:5]=[CH:4][C:3]=1[C:32]#[C:31][CH2:30][OH:33]

Participants

9

Reactant 4

HCID 7859Propargyl alcoholHCID 11776TriphenylphosphineHCID 81531DiisopropylethylamineHCID 27792531,2,3-Trifluoro-4-iodobenzene

Product 1

HCID 59407550HCID 59407550, compound

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 11029508Palladium, tris[mu-[(1,2-eta:4,5-eta)-(1E,4E)-1,5-diphenyl-1,4-pentadien-3-one]]di-, compd. with trichloromethane (1:1)CatalystHCID 8028TetrahydrofuranSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

A mixture of 2,3,4-trifluoroiodobenzene (5.00 g), copper(I) iodide (73.9 mg), triphenylphosphine (254 mg), tris(dibenzylideneacetone)dipalladium(0) chloroform adduct (402 mg), propargyl alcohol (1.26 ml), diisopropylethylamine (13.5 ml) and tetrahydrofuran (100 ml) was stirred at room temperature for 17 hr. The reaction mixture was added to brine, and the mixture was extracted with ethyl acetate, washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The residue 5 was purified by silica gel column chromatography (hexane:ethyl acetate=99:1-80:20) to give the object product (3.14 g) as a brown oil.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washwashed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customThe residue 5 was purified by silica gel column chromatography (hexane:ethyl acetate=99:1-80:20)

Sources & evidence

ORD record
ord-64f354e731d648b5bbc2fe28eab62b41
Source dataset
uspto-grants-2012_03
Patent number
US08129361B2

Reaction notes

Loading…