Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → HCID 69887629, compound

HRID 1954912Notes

Reaction equation

HRID 1954912 reaction equation
[Si]([O:8][CH:9]1[C:17]2[C:12](=[CH:13][C:14]([F:18])=[CH:15][CH:16]=2)/[C:11](=[CH:19]/[C:20]([NH2:22])=[O:21])/[CH2:10]1)(C(C)(C)C)(C)C.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>C(O)C>[F:18][C:14]1[CH:13]=[C:12]2[C:17]([CH:9]([OH:8])[CH2:10]/[C:11]/2=[CH:19]\[C:20]([NH2:22])=[O:21])=[CH:16][CH:15]=1

Participants

4

Reactant 2

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 86753733HCID 86753733, compound

Product 1

HCID 69887629HCID 69887629, compoundYield 62.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of (E)-2-(3-((tert-butyldimethylsilyl)oxy)-6-fluoro-1-indanylidene) acetamide (1.80 g, 5.6 mmoles) and pyridinium p-toluenesulfonate (0.85 g, 3.4 mmoles, Aldrich) in ethanol (65 mL) was heated at 55-68° C. for 3.5 hours under a nitrogen atmosphere and evaporated in vacuo. The residue was dissolved in ethyl acetate (150 mL) and washed successively with water (2×150 mL) and brine (150 mL), dried over magnesium sulfate, filtered and evaporated in vacuo. The residue was chromatographed on silica gel eluting with ethyl acetate. gradually increasing the polarity to ethyl acetate:ethanol (95:5). The fractions containing the major spot were combined and evaporated in vacuo, and the residue was dried in a vacuum at 80° C. for 18 hours to give 0.72 g (62%) of (E)-2-(6-fluoro-3-hydroxy-1-indanylidene)acetamide as a white solid, mp 166-168° C.;

Workup

  1. customevaporated in vacuo
  2. dissolutionThe residue was dissolved in ethyl acetate (150 mL)
  3. washwashed successively with water (2×150 mL) and brine (150 mL)
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. customThe residue was chromatographed on silica gel eluting with ethyl acetate
  8. temperaturegradually increasing the polarity to ethyl acetate:ethanol (95:5)
  9. additionThe fractions containing the major spot
  10. customevaporated in vacuo
  11. customthe residue was dried in a vacuum at 80° C. for 18 hours

Sources & evidence

ORD record
ord-2a61407654a44b589fffcdce79e87365
Source dataset
uspto-grants-2000_09
Patent number
US06124284

Reaction notes

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