Trimethylsilyl iodide → HCID 76684264, compound

HRID 925204Notes

Reaction equation

HRID 925204 reaction equation
C(OC([N:6]1[CH2:21][CH2:20][C:10]2[C:11]3[C:12]([CH3:19])([CH3:18])[CH2:13][CH2:14][C:15]=3[CH:16]=[CH:17][C:9]=2[CH2:8][CH2:7]1)=O)C.[Si](I)(C)(C)C>C(Cl)(Cl)Cl>[CH3:18][C:12]1([CH3:19])[C:11]2[C:10]3[CH2:20][CH2:21][NH:6][CH2:7][CH2:8][C:9]=3[CH:17]=[CH:16][C:15]=2[CH2:14][CH2:13]1

Participants

4

Reactant 2

HCID 85247Trimethylsilyl iodideHCID 86725316HCID 86725316, compound

Product 1

HCID 76684264HCID 76684264, compoundYield 49.7%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
60 °C

Procedure

Into a glass vial containing the product from step (a) (102 mg, 0.355 mmol) in CHCl3 (2 ml), TMSI (483 μL, 3.55 mmol) was added. The reaction mixture was heated to 60° C. for 2 hours. The volatiles were evaporated in vacuo and 2M HCl (5 ml) and water (25 ml) were added. The aqueous mixture was washed with diethyl ether (2×). The aqueous layer was then basified with 2M NaOH to pH 10 and extracted with DCM (3×). The combined DCM extracts were washed with brine, dried over Na2SO4, and solvent evaporated in vacuo to give the title product as a white semi-solid (38 mg). 1H NMR (300 MHz, CDCl3) δ 6.93-6.91 (m, 2H); 3.05-2.89 (m, 8H); 2.80 (t, J=7.5 Hz, 2H); 1.98 (br s, 1H); 1.90 (t, J=7.5 Hz, 2H); 1.35 (s, 6H); MS: ESI (positive): 216 (M+1).

Workup

  1. additionwas added
  2. customThe volatiles were evaporated in vacuo and 2M HCl (5 ml) and water (25 ml)
  3. additionwere added
  4. washThe aqueous mixture was washed with diethyl ether (2×)
  5. extractionextracted with DCM (3×)
  6. washThe combined DCM extracts were washed with brine
  7. dry with materialdried over Na2SO4, and solvent
  8. customevaporated in vacuo

Sources & evidence

ORD record
ord-5856d28abba248e885f8723358d1d135
Source dataset
uspto-grants-2016_03
Patent number
US09284277B2

Reaction notes

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