Lithium iodide → HCID 18448188, compound

HRID 1723907Notes

Reaction equation

HRID 1723907 reaction equation
[CH2:1]([O:5][C:6]1[CH:11]=[CH:10][C:9]([S:12]([O:15][C:16]2[C:25]([CH3:26])=[CH:24][CH:23]=[CH:22][C:17]=2[C:18]([O:20]C)=[O:19])(=[O:14])=[O:13])=[CH:8][CH:7]=1)[C:2]#[C:3][CH3:4].[I-].[Li+]>C(OCC)(=O)C>[CH2:1]([O:5][C:6]1[CH:7]=[CH:8][C:9]([S:12]([O:15][C:16]2[C:25]([CH3:26])=[CH:24][CH:23]=[CH:22][C:17]=2[C:18]([OH:20])=[O:19])(=[O:14])=[O:13])=[CH:10][CH:11]=1)[C:2]#[C:3][CH3:4]

Participants

4

Reactant 2

HCID 66321Lithium iodide2×HCID 18448189HCID 18448189, compound

Product 1

HCID 18448188HCID 18448188, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 0.200 g (0.535 mmol) of the product of Step 1 in 12 mL of ethyl acetate is added 0.716 g (5.35 mmol) of lithium iodide and the resulting mixture is heated to reflux for 24 h. An additional 0.716 g (5.35 mmol) of lithium iodide is then added and the reaction mixture is heated to reflux for an additional 6 h. The reaction is then let cool to room temperature and washed with 5% HCl solution, sodium thiosulfate solution, and brine. The organics are then dried over MgSO4, filtered and concentrated in vacuo to afford 0.123 g (64%) of 2-({[4-(2-butynyloxy)phenyl]sulfonyl}oxy)-3-methylbenzoic acid as a white solid pure enough for use in the next step. Electrospray Mass Spec: 358.8 (M−H)−

Workup

  1. temperaturethe resulting mixture is heated
  2. temperatureto reflux for 24 h
  3. temperaturethe reaction mixture is heated
  4. temperatureto reflux for an additional 6 h
  5. washwashed with 5% HCl solution, sodium thiosulfate solution, and brine
  6. dry with materialThe organics are then dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4501bf419d3c49758995aa392955561f
Source dataset
uspto-grants-2009_02
Patent number
US07485667B2

Reaction notes

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