p-Toluenesulfonic acid monohydrate → HCID 54589357, compound

HRID 1725862Notes

Reaction equation

HRID 1725862 reaction equation
[CH2:1]([O:3][C:4](=[O:17])[CH2:5][C:6]1(O)[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([F:15])[CH:13]=2)[CH2:8][CH2:7]1)[CH3:2].C1(C)C=CC(S(O)(=O)=O)=CC=1.O.[Cl-].[Cl-].[Ca+2]>C1(C)C=CC=CC=1>[CH2:1]([O:3][C:4](=[O:17])[CH2:5][C:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([F:15])[CH:13]=2)[CH2:8][CH:7]=1)[CH3:2]

Participants

5

Reactant 3

HCID 521998p-Toluenesulfonic acid monohydrateHCID 5284359Calcium ChlorideHCID 23293626Ethyl 2-(6-fluoro-1-hydroxy-1-indanyl)acetate2×

Product 1

HCID 54589357HCID 54589357, compoundYield 21.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

The crude (6-Fluoro-1-hydroxy-indan-1-yl)-acetic acid ethyl ester (Compound G in FIG. 7; 3.55 g), p-toluene sulfonic acid•H2O (PTSA; 5.67 g, 29.8 mmol), and CaCl2 (4.13 g, 37.2 mmol) in toluene (66 mL) were refluxed overnight. The solution was filtered and the solid residue washed with benzene. The combined organics were washed with water, NaHCO3, water, dried (MgSO4), filtered, and concentrated in vacuo. Purification using flash chromatography (13:1 hexane/EtOAc) afforded the title compound (Compound H in FIG. 7) as an orange solid (0.703 g). 1H NMR (CDCl3) δ 7.25 (m, 2H), 7.06 (m, 1H), 6.25 (d, J=2.3 Hz, 1H), 4.24 (q, J=7.0 Hz, 2H), 3.32 (s, 2H), 3.03 (s, 2H), 1.33 (t, J=7.1 Hz, 3H); ESI-CID 221 (M-H+).

Workup

  1. filtrationThe solution was filtered
  2. washthe solid residue washed with benzene
  3. washThe combined organics were washed with water, NaHCO3, water
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customPurification

Sources & evidence

ORD record
ord-09492884d2e147b38388e9db07daca1d
Source dataset
uspto-grants-2009_02
Patent number
US07491744B2

Reaction notes

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