3,3-Diethoxypropyne → HCID 19365968, compound

HRID 850115Notes

Reaction equation

HRID 850115 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]([OH:25])([C:16]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1I)=[CH2:17])[CH2:10][N:11]1[CH:15]=[N:14][CH:13]=[N:12]1.[CH2:26]([O:28][CH:29]([O:32][CH2:33][CH3:34])[C:30]#[CH:31])[CH3:27]>C(N(CC)CC)C.O1CCCC1.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>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]([OH:25])([C:16]([C:18]1[CH:23]=[CH:22][C:21]([C:31]#[C:30][CH:29]([O:32][CH2:33][CH3:34])[O:28][CH2:26][CH3:27])=[CH:20][CH:19]=1)=[CH2:17])[CH2:10][N:11]1[CH:15]=[N:14][CH:13]=[N:12]1

Participants

6

Reactant 2

HCID 662853,3-DiethoxypropyneHCID 19365994HCID 19365994, compound

Product 1

HCID 19365968HCID 19365968, compoundYield 60.1%

Reagents, catalysts & solvents 3

HCID 178418476HCID 178418476, compoundCatalystHCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolvent

Procedure

A mixture of 2-(2,4-difluorophenyl)-3-(iodophenyl)-1-(1,2,4-triazol-1-yl)-3-buten-2-ol (4.0 g, 8.8 mmol-see Preparation 20), 3,3-diethyloxyprop-1-yne (1.52 ml, 10.6 mmol), copper(l)iodide (0.02 g) and bis(triphenylphosphine)palladium dichloride (0.12 g) In triethylamine (40 ml) and tetrahydrofuran (13 ml) was stirred at room temperature for 18 hours. The solvents were removed under reduced pressure and the residue was partitioned between dichloromethane (50 ml) and water (50 ml). The organic layer was dried (MgSO4) and evaporated under reduced pressure. The residue was flash chromatographed on silica by elution with ethyl acetate. Fractions containing the desired product were combined and evaporated under reduced pressure to yield 2-(2,4-difluorophenyl)-3-(4-[3,3-diethoxyprop-1-yn-1-yl]phenyl)-1-(1,2,4-triazol-1-yl)-3-buten-2-ol as a yellow gum (2,4 g, 60%). Trituration with cyclohexane gave an off-white solid which was characterised by NMR.

Workup

  1. customThe solvents were removed under reduced pressure
  2. customthe residue was partitioned between dichloromethane (50 ml) and water (50 ml)
  3. dry with materialThe organic layer was dried (MgSO4)
  4. customevaporated under reduced pressure
  5. customchromatographed on silica by elution with ethyl acetate
  6. additionFractions containing the desired product
  7. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-49512498e9434c6b9e16ed2a26231857
Source dataset
uspto-grants-2000_01
Patent number
US06015825

Reaction notes

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