3-Butyn-1-OL → HCID 17756178, compound

HRID 2382552Notes

Reaction equation

HRID 2382552 reaction equation
I[C:2]1[CH:19]=[CH:18][C:5]([CH2:6][N:7]2[C:15](=[O:16])[C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[C:8]2=[O:17])=[CH:4][CH:3]=1.[CH2:20]([OH:24])[CH2:21][C:22]#[CH:23]>[Pd](Cl)Cl.[Cu](I)I.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CN(C=O)C>[OH:24][CH2:20][CH2:21][C:22]#[C:23][C:2]1[CH:19]=[CH:18][C:5]([CH2:6][N:7]2[C:15](=[O:16])[C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[C:8]2=[O:17])=[CH:4][CH:3]=1

Participants

7

Reactant 2

HCID 135663-Butyn-1-OLHCID 17755957HCID 17755957, compound

Product 1

HCID 17756178HCID 17756178, compoundYield 45.2%

Reagents, catalysts & solvents 4

HCID 11776TriphenylphosphineCatalystHCID 24290Palladium ChlorideCatalystHCID 83717Copper iodideCatalystHCID 6228DimethylformamideSolvent

Procedure

To a slurry of 2-(4 iodo-benzyl)-isoindole-1,3-dione (2.0 g, 5.51 mmol), triphenylphosphine (14.4 mg, 0.055 mmol), and palladium chloride (5 mg, 0.028 mmol) in DEA (20 mL) was added DMF (4 mL) and copper iodide (11 mg, 0.055 mmol) followed by 3-butyn-1-ol (417 μL, 5.51 mmol). The reaction stirred at room temperature overnight under nitrogen atmosphere. The next day, the reaction mixture was concentrated and purified by flash column chromatography (2:1 Hexane:ethyl acetate) to yield the product as a yellow solid (0.76 g, 45% yield). 1H NMR (600 MHz, CDCl3): δ 7.86 (m, 2H), 7.76 (m, 2H), 7.36 (s, 4H), 4.83 (s, 2H), 3.80 (q, 2H, J=6.3 Hz), 2.68 (t, 2H, J=6.2 Hz), 1.80 (t, 1H, J=6.4 Hz); 13C NMR (150 MHz, CDCl3): δ 167.5, 135.5, 133.6, 131.5, 131.4, 128.0, 122.9, 122.5, 86.3, 81.5, 60.6, 40.8, 23.3.

Workup

  1. concentrationThe next day, the reaction mixture was concentrated
  2. custompurified by flash column chromatography (2:1 Hexane:ethyl acetate)

Sources & evidence

ORD record
ord-318f3c8bb7714b0cbef63d848eeefe74
Source dataset
uspto-grants-2012_09
Patent number
US08263042B2

Reaction notes

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