Water → HCID 18969714, compound

HRID 399083Notes

Reaction equation

HRID 399083 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:9](O)[CH2:10][C:11]2[CH:16]=[CH:15][C:14]([S:17][CH3:18])=[CH:13][CH:12]=2)[CH:5]=[CH:6][C:7]=1[F:8].CC1C=CC(S(O)(=O)=O)=CC=1.O>C1(C)C=CC=CC=1>[CH3:18][S:17][C:14]1[CH:13]=[CH:12][C:11](/[CH:10]=[CH:9]/[C:4]2[CH:5]=[CH:6][C:7]([F:8])=[C:2]([F:1])[CH:3]=2)=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 53736244HCID 53736244, compound

Product 1

HCID 18969714HCID 18969714, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

The alcohol from step 3 (3.78 g) was dissolved in toluene (45 mL) and p-TsOH (260 mg) was added. The mixture was refluxed with azeotropic removal of water for 18 hr, cooled to r.t., washed with saturated NaCHO3 sol., brine, dried (MgSO4) and the solvent evaporated. The residue was purified by flash chromatography (silica gel; hexane/EtOAc (95:5)) to give the title product as a yellow oil.

Workup

  1. washwashed with saturated NaCHO3 sol., brine
  2. dry with materialdried (MgSO4)
  3. customthe solvent evaporated
  4. customThe residue was purified by flash chromatography (silica gel; hexane/EtOAc (95:5))

Sources & evidence

ORD record
ord-1632d3039bf048258ec3654f384b36ae
Source dataset
uspto-grants-1998_10
Patent number
US05817700

Reaction notes

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