Water → HCID 54589357, compound

HRID 1919620Notes

Reaction equation

HRID 1919620 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

6

Reactant 4

HCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 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-0f664a36b4fd42aaa9ba9ba069778d6b
Source dataset
uspto-grants-2012_05
Patent number
US08168656B2

Reaction notes

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