Iodine → HCID 18782545, compound

HRID 1420859Notes

Reaction equation

HRID 1420859 reaction equation
[I:1]I.[C:3]([C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=1)#[N:4].C(=O)([O-])O.[Na+].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH3:36][O:37][C:38]1[CH:45]=[CH:44][C:41]([CH2:42]O)=[CH:40][CH:39]=1.N(C(OCC)=O)=NC(OCC)=O>O>[I:1][C:7]1[CH:6]=[C:5]([CH:10]=[CH:9][C:8]=1[O:11][CH2:42][C:41]1[CH:44]=[CH:45][C:38]([O:37][CH3:36])=[CH:39][CH:40]=1)[C:3]#[N:4]

Participants

8

Reactant 6

HCID 807IodineHCID 77384-Methoxybenzyl alcoholHCID 11776TriphenylphosphineHCID 130194-CyanophenolHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 516892Sodium Bicarbonate2×

Product 1

HCID 18782545HCID 18782545, compoundYield 15.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Iodine (21. g, 84 mmol) was added to a solution of 4-cyanophenol (10.0 g, 84 mmol) and sodium hydrogen carbonate (7.06 g, 84 mmol) in water (100 mL) and the mixture was stirred at room temperature for 24 h. The solid was collected, washed with water and dried in vacuo. The solid was dissolved in tetrahydrofuran (100 mL) and triphenylphosphine (14.4 g, 55 mmol) and 4-methoxybenzyl alcohol (8.3 g, 60 mmol) were added. Diethyl azodicarboxylate (8.5 mL, 55 mmol) was added slowly and the mixture was stirred at room temperature for 16 h. The mixture was poured into sodium hydrogen carbonate solution (saturated, 200 mL) and extracted with ethyl acetate (2×200 mL). The combined organic fractions were dried (MgSO4) and the solvent was evaporated under reduced pressure. The residue was purified by flash column chromatography on silica gel to give the title compound (3.38 g). 1H NMR (250 MHz, CDCl3) δ 8.05 (1H, d, J 2.0 Hz), 7.57 (1H, dd, J 2.0, 8.5 Hz), 7.38 (2H, d, J 6.8 Hz), 6.79-6.96 (3H, m), 5.14 (2H, s), and 3.82 (3H, s).

Workup

  1. customThe solid was collected
  2. washwashed with water
  3. customdried in vacuo
  4. dissolutionThe solid was dissolved in tetrahydrofuran (100 mL)
  5. stirringthe mixture was stirred at room temperature for 16 h
  6. extractionextracted with ethyl acetate (2×200 mL)
  7. dry with materialThe combined organic fractions were dried (MgSO4)
  8. customthe solvent was evaporated under reduced pressure
  9. customThe residue was purified by flash column chromatography on silica gel

Sources & evidence

ORD record
ord-f8c535a4758d4cf4a164825ba43ef150
Source dataset
uspto-grants-2000_06
Patent number
US06071927

Reaction notes

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