Imidazole → HCID 67206760, compound

HRID 1023852Notes

Reaction equation

HRID 1023852 reaction equation
[I:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:10]O.[NH:12]1[CH:16]=[CH:15][N:14]=[CH:13]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[I:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:10][N:12]1[CH:16]=[CH:15][N:14]=[CH:13]1

Participants

6

Reactant 4

HCID 795ImidazoleHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 19696487HCID 19696487, compound

Product 1

HCID 67206760HCID 67206760, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (2-iodo-3-methoxyphenyl)methanol (0.350 g, 1.33 mmol), (Organic Letters, 2001, vol. 3, #21 p. 3245-3248) imidazole (0.181 g, 2.65 mmol) and triphenyl phosphine (0.382 g, 1.46 mmol) in tetrahydrofuran (5 mL) at 0° C. was added Diethyl azodicarboxylate (40% solution in toluene; 0.664 mL). The yellow solution was allowed to warm to room temperature and stirred at 60° C. overnight. After evaporating the solvent under reduced pressure, the crude was purified by column chromatography (5% EtOAc:hexanes, 20% EtOAc; Hexanes). Yield=43%. 1H NMR: 3.90 (s, 3H), 5.19 (s, 2H), 6.43 (d, 1H, J=5.70 Hz), 6.77 (d, 1H, J=6.09 Hz), 6.93 (s, 1H), 7.10 (s, 1H), 7.24 (t, 1H, J=6.03 Hz)

Workup

  1. customAfter evaporating the solvent under reduced pressure
  2. customthe crude was purified by column chromatography (5% EtOAc:hexanes, 20% EtOAc; Hexanes)

Sources & evidence

ORD record
ord-de68a19ac0534164a740fad90748927b
Source dataset
uspto-grants-2014_05
Patent number
US08722720B2

Reaction notes

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