Imidazole → 1,1'-((1,1-Dimethylethyl)((5-iodopentyl)oxy)silylene)bis(benzene)

HRID 2275438Notes

Reaction equation

HRID 2275438 reaction equation
N1C=CN=C1.[I:6]I.[Si:8]([O:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30]O)([C:21]([CH3:24])([CH3:23])[CH3:22])([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>C(Cl)Cl>[C:21]([Si:8]([O:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][I:6])([C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)([CH3:23])([CH3:24])[CH3:22]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 807IodineHCID 11776TriphenylphosphineHCID 10925936HCID 10925936, compound

Product 1

HCID 100039911,1'-((1,1-Dimethylethyl)((5-iodopentyl)oxy)silylene)bis(benzene)Yield 92%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Imidazole (310 mg, 4.40 mmol), iodine (440 mg, 3.5 mmol), and a solution of 2 (1 g, 2.98 mmol) in CH2Cl2 (2 mL) were added sequentially to a 0° C. solution of PPh3 (450 mg, 3.5 mmol) in CH2Cl2 (15 mL) and kept in the dark. After 2 h, the reaction mixture was quenched by adding 20% aq. Na2S2O3 (5 mL). The aqueous layer was extracted with CH2Cl2 (2×50 mL). The combined organic extracts were washed with brine (30 mL), dried over anhydrous Na2SO4, and the solvent was removed in vacuo. The residue was purified by careful column chromatography using 5% EtOAC/hexane to afford iodide 3 (1.25 mg, 92%). TLC: 10% EtOAc/hexane, Rf˜0.85; 1H NMR (CDCl3, 400 MHz) δ 7.67-7.62 (m, 4H), 7.45-7.35 (m, 6H), 3.67 (t, 2H, J=6.0 Hz), 3.41 (t, 2H, J=6.7 Hz), 2.03-1.93 (m, 2H), 1.72-1.64 (m, 4H), 1.04 (s, 9H).

Workup

  1. customthe reaction mixture was quenched
  2. additionby adding 20% aq. Na2S2O3 (5 mL)
  3. extractionThe aqueous layer was extracted with CH2Cl2 (2×50 mL)
  4. washThe combined organic extracts were washed with brine (30 mL)
  5. dry with materialdried over anhydrous Na2SO4
  6. customthe solvent was removed in vacuo
  7. customThe residue was purified by careful column chromatography

Sources & evidence

ORD record
ord-580e2615de5442749d739c172376ceef
Source dataset
uspto-grants-2015_09
Patent number
US09127027B2

Reaction notes

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