Imidazole → Mfnmcjgjwprwcp-uhfffaoysa-

HRID 130524Notes

Reaction equation

HRID 130524 reaction equation
O[CH2:2][CH:3]1[CH2:7][N:6]([CH2:8][C:9]2[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=2)[C:5](=[O:17])[CH2:4]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N1C=CN=C1.[I:42]I.S([O-])([O-])(=O)=S.[Na+].[Na+]>C1(C)C=CC=CC=1>[I:42][CH2:2][CH:3]1[CH2:7][N:6]([CH2:8][C:9]2[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=2)[C:5](=[O:17])[CH2:4]1

Participants

7

Reactant 5

HCID 795ImidazoleHCID 807IodineHCID 11776TriphenylphosphineHCID 24477Sodium ThiosulfateHCID 134225594-(Hydroxymethyl)-1-[(4-methoxyphenyl)methyl]pyrrolidin-2-one

Product 1

HCID 11824137Mfnmcjgjwprwcp-uhfffaoysa-

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To alcohol 80 (12.9 g, 0.055 mol) in PhMe was added triphenylphosphine (20 g, 0.077 mol), imidazole (10.8 g, 0.16 mol), and iodine (19 g, 0.075 mol). The suspension was stirred at room temperature 5 hours. A saturated aqueous solution of sodium thiosulphate was added and the two layers separated. The aqueous phase was extracted with ether and the combined organic phases washed with brine, dried (MgSO4) and concentrated. Flash chromatography (6:1 to 4:1 toluene/acetone) of the residue gave iodide 81 as an oil. 11.9 g, 63%. MS, m/z (relative intensity): 346 [M+H, 100%].

Workup

  1. customthe two layers separated
  2. extractionThe aqueous phase was extracted with ether
  3. washthe combined organic phases washed with brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-fcee646bfa31421bae6ca144eeeb9491
Source dataset
uspto-grants-2008_06
Patent number
US07381747B2

Reaction notes

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