Pyridine → 3-(2-Hydroxy-4-methoxyphenyl)-1-(3,4-methylenedioxyphenyl)-5-(prop-1-yloxy)indane

HRID 2288171Notes

Reaction equation

HRID 2288171 reaction equation
COC[O:4][C:5]1[CH:10]=[C:9]([O:11][CH3:12])[CH:8]=[CH:7][C:6]=1[CH:13]1[C:21]2[C:16](=[CH:17][CH:18]=[C:19]([O:22][CH2:23][CH2:24][CH3:25])[CH:20]=2)[CH:15]([C:26]2[CH:31]=[CH:30][C:29]3[O:32][CH2:33][O:34][C:28]=3[CH:27]=2)[CH:14]1C(O)=O.N1C=CC=CC=1.S(Cl)(Cl)=O.SC1C=CC=C[N+]=1[O-]>ClCCl>[OH:4][C:5]1[CH:10]=[C:9]([O:11][CH3:12])[CH:8]=[CH:7][C:6]=1[CH:13]1[C:21]2[C:16](=[CH:17][CH:18]=[C:19]([O:22][CH2:23][CH2:24][CH3:25])[CH:20]=2)[CH:15]([C:26]2[CH:31]=[CH:30][C:29]3[O:32][CH2:33][O:34][C:28]=3[CH:27]=2)[CH2:14]1

Participants

6

Reactant 4

HCID 1049PyridineHCID 24386Thionyl ChlorideHCID 187038773-(4-Methoxy-2-methoxymethoxyphenyl)-1-(3,4-methylenedioxyphenyl)-5-(prop-1-yloxy)indane-2-carboxylic acidHCID 178526253HCID 178526253, compound

Product 1

HCID 217130923-(2-Hydroxy-4-methoxyphenyl)-1-(3,4-methylenedioxyphenyl)-5-(prop-1-yloxy)indaneYield 46%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of (1RS,2SR,3RS)-3-[2-(methoxymethoxy)-4-methoxyphenyl]-1-(3,4-methylenedioxyphenyl)-5-(prop-1-yloxy)indane-2-carboxylic acid (0.2 g, 0.39 mmol) in dichloromethane (4 ml) and pyridine (28 μl, 1.6 mmol) was cooled to 0° C. under argon. To this solution was added thionyl chloride (60 μl, 0.8 mmol). The mixture was allowed to warm to ambient temperature over 20 min. and the volatiles removed in vacuo. The residue was redissolved in toluene and evaporated-in vacuo (twice). The residue was dissolved in dichioromethane (4 ml) and triethylamine (250 μl) added. To this solution at room temperature under argon was added 2-mercaptopyridine-N-oxide (120 mg, 0.8 mmol) dissolved in dichloromethane (1 ml). After strrring for 20 min at room termperature t-butylthiol (450 μl, 4 mmol) was added and the mixture irradiated for 20 min (150 watt spotlight). The volatiles were removed in vacuo and the product partitioned between ethyl acetate and 3 M-aq. HCl. The organic extract was washed with water, sat. aq. NaHCO3 solution and finally brine. After drying (MgSO4 anhydrous), the product was filtered and evaporated. Purification by column chromatography gave the title compound (0.075 g, 41%).

Workup

  1. customthe volatiles removed in vacuo
  2. dissolutionThe residue was redissolved in toluene and evaporated-in vacuo (twice)
  3. dissolutionThe residue was dissolved in dichioromethane (4 ml)
  4. additiontriethylamine (250 μl) added
  5. additionwas added
  6. customthe mixture irradiated for 20 min (150 watt spotlight)
  7. customThe volatiles were removed in vacuo
  8. customthe product partitioned between ethyl acetate and 3 M-aq
  9. extractionThe organic extract
  10. washwas washed with water, sat. aq. NaHCO3 solution and finally brine
  11. dry with materialAfter drying (MgSO4 anhydrous)
  12. filtrationthe product was filtered
  13. customevaporated
  14. customPurification by column chromatography

Sources & evidence

ORD record
ord-06bd981719e44adf8398af58ac428444
Source dataset
uspto-grants-2000_07
Patent number
US06087389

Reaction notes

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