p-Toluenesulfonic acid → HCID 67057742, compound

HRID 604635Notes

Reaction equation

HRID 604635 reaction equation
[F:1][C:2]1[C:7]([CH:8]([CH3:10])[CH3:9])=[CH:6][C:5]([C:11]2[CH:19]=[C:18]3[C:14]([C:15](O)([CH3:20])[CH2:16][CH2:17]3)=[CH:13][C:12]=2[C:22]([O:24][CH3:25])=[O:23])=[C:4]([O:26][CH3:27])[CH:3]=1.CC1C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1.CCOC(C)=O>[F:1][C:2]1[C:7]([CH:8]([CH3:10])[CH3:9])=[CH:6][C:5]([C:11]2[CH:19]=[C:18]3[C:14]([C:15]([CH3:20])=[CH:16][CH2:17]3)=[CH:13][C:12]=2[C:22]([O:24][CH3:25])=[O:23])=[C:4]([O:26][CH3:27])[CH:3]=1

Participants

5

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 67057701HCID 67057701, compound

Product 1

HCID 67057742HCID 67057742, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of methyl 6-(4-fluoro-5-isopropyl-2-methoxyphenyl)-3-hydroxy-3-methylindane-5-carboxylate (22.6 mg, 0.061 mmol) in toluene (1 mL) at room temperature was added TsOH (5.8 mg, 0.030 mmol). The reaction mixture was heated at 80° C. for 1.5 h. The reaction mixture was diluted with EtOAc. The organic layer was washed consecutively with sat. aq. NaHCO3 (1×) and brine (1×), dried (Na2SO4), filtered and concentrated in vacuo to give methyl 6-(4-fluoro-5-isopropyl-2-methoxyphenyl)-3-methyl-1H-indene-5-carboxylate. LCMS calc.=377.2; found=376.9 (M+Na)+. 1H NMR (500 MHz, CDCl3): δ 7.85 (s, 1H); 7.41 (s, 1H); 7.14 (d, J=8.7 Hz, 1H); 6.63 (d, J=12.1 Hz, 1H); 6.30 (t, J=1.5 Hz, 1H); 3.72 (s, 3H); 3.72 (s, 3H); 3.42 (d, J=1.5 Hz, 2H); 3.29-3.21 (m, 1H); 2.25 (s, 3H); 1.31 (d, J=6.9 Hz, 6H).

Workup

  1. washThe organic layer was washed consecutively with sat. aq. NaHCO3 (1×) and brine (1×)
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f697a7b0a3704cfd817909cacbbb8754
Source dataset
uspto-grants-2011_03
Patent number
US07910592B2

Reaction notes

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