Water → HCID 86702663, compound

HRID 513330Notes

Reaction equation

HRID 513330 reaction equation
C(N([CH2:6][CH3:7])CC)C.[C:8](Cl)(=[O:15])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.O.[CH2:18]1[CH2:22]O[CH2:20][CH2:19]1>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>[C:9]1([C:8](=[O:15])[C:20]#[C:19][CH2:18][CH2:22][CH2:14]/[CH:13]=[CH:12]/[C:7]2[CH:6]=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

7

Reactant 4

HCID 962WaterHCID 7412Benzoyl chlorideHCID 8028Tetrahydrofuran2×HCID 8471Triethylamine

Product 1

HCID 86702663HCID 86702663, compoundYield 71%

Reagents, catalysts & solvents 2

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

Procedure

(Cacchi, S. et al. Org. Lett. 2008, 10, 2629) To a flame-dried two-neck 10 mL round-bottomed flask equipped with an argon inlet adapter, a septum, and a stir bar was added PdCl2(PPh3)2 (0.012 g, 0.017 mmol), THF (3 mL), triethylamine (0.14 mL, 1.03 mmol), and benzoyl chloride (0.12 mL, 1.03 mmol). The solution was stirred for 10 min at rt, and copper(I) iodide (0.007 g, 0.034 mmol) was added all at once through the sidearm turning the reaction from cloudy yellow to clear orange. The reaction was stirred for 10 min, and enyne S1 (0.146 g, 0.86 mmol) in THF (0.5 mL) was added all at once via syringe. The reaction was stirred for 3 h until complete by TLC, in which time the reaction became cloudy and yellow. Water was added to the reaction, and the aqueous layer was separated and extracted with ethyl acetate (2×). The combined organic layers were washed with 1 M hydrochloric acid, sat'd aq ammonium chloride, and brine, dried over magnesium sulfate, gravity filtered, and concentrated under reduced pressure. The crude product was purified by silica gel column chromatography (25 g silica cartridge, 0-10% ethyl acetate/hexanes) to yield product 5e as a yellow oil (0.168 g, 71%).

Workup

  1. custom(Cacchi, S. et al. Org. Lett. 2008, 10, 2629) To a flame-dried two-neck 10 mL round-bottomed flask equipped with an argon inlet adapter
  2. customthe reaction from cloudy yellow to clear orange
  3. stirringThe reaction was stirred for 10 min
  4. stirringThe reaction was stirred for 3 h until complete by TLC
  5. customthe aqueous layer was separated
  6. extractionextracted with ethyl acetate (2×)
  7. washThe combined organic layers were washed with 1 M hydrochloric acid
  8. dry with materialdried over magnesium sulfate, gravity
  9. filtrationfiltered
  10. concentrationconcentrated under reduced pressure
  11. customThe crude product was purified by silica gel column chromatography (25 g silica cartridge, 0-10% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-7da832ddc1ff4fef986bd3c2fb60d49d
Source dataset
uspto-grants-2015_08
Patent number
US09102703B2

Reaction notes

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