Water → HCID 18400249, compound

HRID 1019231Notes

Reaction equation

HRID 1019231 reaction equation
[CH:1]([C:4]1[CH:14]=[CH:13][C:12]([CH:15]=[CH:16][O:17]C)=[CH:11][C:5]=1[C:6]([O:8][CH2:9][CH3:10])=[O:7])([CH3:3])[CH3:2].O.I>CC#N.CCOC(C)=O>[CH:1]([C:4]1[CH:14]=[CH:13][C:12]([CH2:15][CH:16]=[O:17])=[CH:11][C:5]=1[C:6]([O:8][CH2:9][CH3:10])=[O:7])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 962WaterHCID 24841Hydrogen iodideHCID 59921282HCID 59921282, compound

Product 1

HCID 18400249HCID 18400249, compoundYield 100.5%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

Compound 1 (25.62 g, 103.2 mmol) was dissolved in CH3CN (370 mL) at room temperature under nitrogen. H2O (15.5 mL) and a 57% aqueous solution of HI (14.7 mL) were added. The reaction solution was stirred at room temperature for 1 hour, and then was diluted with EtOAc (1000 mL), washed with H2O (400 mL), 0.25N Na2S2O3 (400 mL), H2O (400 mL), and saturated aqueous NaCl (400 mL), dried over Na2SO4, filtered, evaporated, and dried under vacuum to afford 24.31 g (100%) of Compound 2 as a yellow oil, which was used without further purification. The following values were obtained by nuclear magnetic resonance spectroscopy:

Workup

  1. washwashed with H2O (400 mL), 0.25N Na2S2O3 (400 mL), H2O (400 mL), and saturated aqueous NaCl (400 mL)
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. customevaporated
  5. customdried under vacuum

Sources & evidence

ORD record
ord-e7c831c305534066ab13bc202467cf00
Source dataset
uspto-grants-2002_11
Patent number
US06486202B1

Reaction notes

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