Imidazole → HCID 67484514, compound

HRID 1992796Notes

Reaction equation

HRID 1992796 reaction equation
O[CH2:2][C:3]1[CH:17]=[CH:16][C:6]([O:7][CH2:8][CH2:9][CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:5][CH:4]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N1C=CN=C1.[I:42]I>C(#N)C>[I:42][CH2:2][C:3]1[CH:17]=[CH:16][C:6]([O:7][CH2:8][CH2:9][CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 795ImidazoleHCID 807IodineHCID 11776TriphenylphosphineHCID 22340602Butanoic acid, 4-[4-(hydroxymethyl)phenoxy]-, ethyl ester

Product 1

HCID 67484514HCID 67484514, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of the intermediate from step B (1 g, 4.24 mmol) in acetonitrile was added triphenyl phosphine (1.45 g, 5.5 mmol), imidazole (0.4 g, 5.93 mmol) and iodine (1.51 g, 5.94 mmol). After 20 minutes, the reaction was quenched with saturated Na2S2O3 solution. The resulting mixture was extracted with ethyl acetate washed with brine and dried over anhydrous Na2SO4. The solution was filtered, concentrated in vacuo and purified by flash chromatography using 15% ethyl acetate-hexanes to give the desired product as an oil. 1H NMR (CDCl3, 500 MHz): 7.32 (d, J=8.7 Hz, 2H), 6.82 (d, J=8.7 Hz, 2H), 4.48 (s, 2H), 4.18 (q, J=6.1 Hz, 2H), 4.01 (t, J=6.1 Hz, 2H), 2.53 (t, J=7.4 Hz, 2H), 2.14 (m, 2H), 1.29 (t, J=7.1 Hz, 3H). LC-MS=2.36 min; (M+23)=371.0.

Workup

  1. customthe reaction was quenched with saturated Na2S2O3 solution
  2. extractionThe resulting mixture was extracted with ethyl acetate
  3. washwashed with brine
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationThe solution was filtered
  6. concentrationconcentrated in vacuo
  7. custompurified by flash chromatography

Sources & evidence

ORD record
ord-285be01c5d95428494f37f336f6f9638
Source dataset
uspto-grants-2010_01
Patent number
US07649009B2

Reaction notes

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