4-Pentyn-1-ol → HCID 57516936, compound

HRID 1944868Notes

Reaction equation

HRID 1944868 reaction equation
[F:1][C:2]([F:15])([F:14])[C:3]([N:5]([C:7]1[CH:12]=[CH:11][C:10](I)=[CH:9][CH:8]=1)[CH3:6])=[O:4].[CH2:16]([OH:21])[CH2:17][CH2:18][C:19]#[CH:20]>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.[Cu]I>[F:1][C:2]([F:15])([F:14])[C:3]([N:5]([C:7]1[CH:12]=[CH:11][C:10]([C:20]#[C:19][CH2:18][CH2:17][CH2:16][OH:21])=[CH:9][CH:8]=1)[CH3:6])=[O:4]

Participants

5

Reactant 2

HCID 793464-Pentyn-1-olHCID 210712382,2,2-trifluoro-N-(4-iodophenyl)-N-methylacetamide

Product 1

HCID 57516936HCID 57516936, compound

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalyst

Procedure

Intermediate 33 (0.377 g, 1.147 mmol) in 10 mL of TEA was combined with PdCl2(PPh3)2 (0.02294 mmol, 0.016 g) the mixture was then degassed using N2 for 5 minutes. Then CuI (0.01147 mmol, 0.002 g) and Pent-4-yn-1-ol (1.147 mmol, 0.115 g) then reacted at 50° C. for 4 hours. The reaction was worked up quenching the reaction with 1× saturated NaHCO3, extracted 4×25 ml EtOAc then washed 1× water, 1× saturated NaCl, dried over Na2SO4, then concentrated. The product was purified 0-75% EtOAc in Hexanes over 20 min on silica. ES/MS calcd. for C14H14F3NO2 285.1. Found m/z=286 (M+H)+.

Workup

  1. customwas then degassed
  2. customfor 5 minutes
  3. customThe reaction was worked up quenching
  4. customthe reaction with 1× saturated NaHCO3
  5. extractionextracted 4×25 ml EtOAc
  6. washthen washed 1× water, 1× saturated NaCl
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated
  9. customThe product was purified 0-75% EtOAc in Hexanes over 20 min on silica

Sources & evidence

ORD record
ord-5f5a1497357b40aeacd002c517c79faa
Source dataset
uspto-grants-2013_03
Patent number
US08394829B2

Reaction notes

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