Imidazole → HCID 67300712, compound

HRID 1015462Notes

Reaction equation

HRID 1015462 reaction equation
[I:1]I.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N1C=CN=C1.O[CH2:28][CH2:29][CH2:30][C:31]1[S:35][C:34]([C:36]([O:38][CH3:39])=[O:37])=[CH:33][CH:32]=1>C(Cl)Cl>[I:1][CH2:28][CH2:29][CH2:30][C:31]1[S:35][C:34]([C:36]([O:38][CH3:39])=[O:37])=[CH:33][CH:32]=1

Participants

6

Reactant 4

HCID 795ImidazoleHCID 807IodineHCID 11776TriphenylphosphineHCID 10608090Methyl 5-(3-hydroxypropyl)thiophene-2-carboxylate

Product 1

HCID 67300712HCID 67300712, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Iodine (187 mg, 0.74 mmol) was added to a solution of triphenylphosphine (194 mg, 0.74 mmol) and imidazole (49 mg, 0.74 mmol) in CH2Cl2 (1.5 mL) at 23° C. After 0.5 h a solution of methyl 5-(3-hydroxypropyl)thiophene-2-carboxylate 7 (123 mg, 0.62 mmol) in CH2Cl2 (0.5 mL) was added. After stirring for 2 h the reaction was concentrated in vacuo and the residue was purified by FCC (silica gel, 7:3 hex/EtOAc) to provide 170 mg (89%) of the iodide 108.

Workup

  1. concentrationwas concentrated in vacuo
  2. customthe residue was purified by FCC (silica gel, 7:3 hex/EtOAc)

Sources & evidence

ORD record
ord-fbd2b055981c40ecb425bf4f46ffe70d
Source dataset
uspto-grants-2011_07
Patent number
US07985767B2

Reaction notes

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