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

HRID 650776Notes

Reaction equation

HRID 650776 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.S(Cl)(Cl)=O.SC1C=CC=C[N+]=1[O-]>ClCCl.N1C=CC=CC=1>[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 3

HCID 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 2

HCID 1049PyridineSolventHCID 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 pl, 1.6 mmnol) 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 dichloromethane (4 ml) and triethylarmine (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 stirring for 20 min at room terrnperature 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 3M-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
  3. customevaporated in vacuo (twice)
  4. dissolutionThe residue was dissolved in dichloromethane (4 ml)
  5. additiontriethylarmine (250 μl) added
  6. additionwas added
  7. customthe mixture irradiated for 20 min (150 watt spotlight)
  8. customThe volatiles were removed in vacuo
  9. customthe product partitioned between ethyl acetate and 3M-aq
  10. extractionThe organic extract
  11. washwas washed with water, sat. aq. NaHCO3 solution and finally brine
  12. dry with materialAfter drying (MgSO4 anhydrous)
  13. filtrationthe product was filtered
  14. customevaporated
  15. customPurification by column chromatography

Sources & evidence

ORD record
ord-2eb50c6ef6b94b63ba314129692efa4f
Source dataset
uspto-grants-2001_08
Patent number
US06274737B1

Reaction notes

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