Imidazole → HCID 58052362, compound

HRID 2190189Notes

Reaction equation

HRID 2190189 reaction equation
O[CH2:2][CH2:3][O:4][CH2:5][C:6]([CH3:12])([CH3:11])[C:7]([O:9][CH3:10])=[O:8].N1C=CN=C1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[I:37]I>C(Cl)Cl>[I:37][CH2:2][CH2:3][O:4][CH2:5][C:6]([CH3:12])([CH3:11])[C:7]([O:9][CH3:10])=[O:8]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 807IodineHCID 11776TriphenylphosphineHCID 58052550HCID 58052550, compound

Product 1

HCID 58052362HCID 58052362, compoundYield 99.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of methyl 3-(2-hydroxyethoxy)-2,2-dimethylpropanoate (2.30 g, 1 eq.), 1H-imidazole (1.07 g, 1.2 eq.) and DCM (100 ml) was slowly added resin-bound triphenylphosphine (1.2 eq.) and iodine (3.98 g, 1.2 eq.). The reaction mixture was stirred at room temperature overnight and filtered. The filtrate was concentrated and subject to silica gel chromatography using 0-25% ether-heptane to yield the title compound as a colorless oil (3.73 g, 62%).

Workup

  1. filtrationfiltered
  2. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-1d7ed12c55e440dabea210398c6a5936
Source dataset
uspto-grants-2012_12
Patent number
US08324239B2

Reaction notes

Loading…