Imidazole → (4-Iodo-but-2-ynyloxy)-acetonitrile

HRID 349369Notes

Reaction equation

HRID 349369 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[I:20]I.O[CH2:23][C:24]#[C:25][CH2:26][O:27][CH2:28][C:29]#[N:30].N1C=CN=C1>C(Cl)Cl>[I:20][CH2:23][C:24]#[C:25][CH2:26][O:27][CH2:28][C:29]#[N:30]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 807IodineHCID 11776TriphenylphosphineHCID 86012515(4-Hydroxy-but-2-ynyloxy)-acetonitrile

Product 1

HCID 86012516(4-Iodo-but-2-ynyloxy)-acetonitrileYield 92%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Triphenylphosphine (10.94 g, 41.7 mmol) and iodine (10.55 g, 41.6 mmol were added sequentially to a solution of (4-hydroxy-but-2-ynyloxy)-acetonitrile (4.35 g, 34.8 mmol) in CH2Cl2 (100 mL). The reaction mixture became homogeneous after 5 min at rt and imidazole (2.76 g, 40.5 mmol) was added slowly in small portions. After 1.5 h at rt, the reaction was filtered through activity I basic alumina, washing with 20% EtOAc/Hexane. The filtrate was concentrated in vacuo then purified by flash column chromatography on silica gel (hexane→10% EtOAc/hexane, gradient) to afford 7.51 g (92%) of (4-iodo-but-2-ynyloxy)-acetonitrile.

Workup

  1. waitAfter 1.5 h at rt
  2. filtrationthe reaction was filtered through activity I basic alumina
  3. washwashing with 20% EtOAc/Hexane
  4. concentrationThe filtrate was concentrated in vacuo
  5. customthen purified by flash column chromatography on silica gel (hexane→10% EtOAc/hexane, gradient)

Sources & evidence

ORD record
ord-9b79928d940f40fb95dddc7f4bb9f9ef
Source dataset
uspto-grants-2007_02
Patent number
US07179820B2

Reaction notes

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