Tin tetrachloride → trans-1-(5-Ethyl-2-furanyl)-1,2,3,4-tetrahydro-6,7-methylenedioxy-naphthalene-2-carboxylic acid

HRID 235109

Reaction equation

HRID 235109 reaction equation
[Li+].CC([N-]C(C)C)C.[CH2:9]1[O:17][C:16]2[CH:15]=[CH:14][C:13]([CH2:18][CH2:19][CH2:20][C:21]([O:23]C)=[O:22])=[CH:12][C:11]=2[O:10]1.[CH2:25]([C:27]1[O:31][C:30]([CH:32]=O)=[CH:29][CH:28]=1)[CH3:26].Cl[Sn](Cl)(Cl)Cl>C1COCC1.C(Cl)Cl>[CH2:25]([C:27]1[O:31][C:30]([C@@H:32]2[C:14]3[C:13](=[CH:12][C:11]4[O:10][CH2:9][O:17][C:16]=4[CH:15]=3)[CH2:18][CH2:19][C@H:20]2[C:21]([OH:23])=[O:22])=[CH:29][CH:28]=1)[CH3:26]

Participants

7

Reactant 4

HCID 24287Tin tetrachlorideHCID 899895-Ethyl-2-furaldehydeHCID 529781Methyl 4-(3,4-methylenedioxyphenyl)butanoateHCID 2724682Lithium diisopropylamide

Product 1

HCID 22869412trans-1-(5-Ethyl-2-furanyl)-1,2,3,4-tetrahydro-6,7-methylenedioxy-naphthalene-2-carboxylic acid

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
0 °C

Procedure

To a freshly prepared solution of LDA (15 mmol) in 30 mL of THF cooled to -78° C. was added a solution of 3,4-methylenedioxybenzenebutanoic acid, methyl ester (14 mmol), from step 558 above, in 10 mL of THF. The solution was stirred for 5 minutes, and a solution of 5-ethylfuran-2-carboxaldehyde (13.8 mmol), from step 55b above, in 30 mL of THF was added. The reaction mixture was warmed to 0° C., and the reaction was quenched with 10 mL of satd NH4Cl. The organic layer was separated, and the aqueous layer was extracted with ether. The organic layers were combined, dried and concentrated. The residue was dissolved in 50 mL of methylene chloride, and the solution was cooled to 0° C. To this solution was added a solution of SnCl4 (1M, 13 mmol) in methylene chloride, and the reaction mixtrue was stirred for 5 minutes. The reaction was quenched with 1 N HCl (10 mL). The organic layer was separated, and the aqueous layer was extracted with methylene chloride. The organic layers were combined, dried, filtered and concentrated. The crude methyl ester intermediate was hydrolyzed with KOH in methanol by standard procedures, and the title product was isolated (3.04 g). NMR (CDCl3) δ:6.56 (s, 1H), 6.54 (s, 1H), 5.91-5.81 (m, 4H), 4.39 (d, J=7 Hz, 1H), 3.13 (m, 1H), 2.80 (t, J=7 Hz, 2H), 2.59 (q, J=8 Hz, 2H), 2.18-1.96 (m, 2H), 1.20 (t, J=8 Hz, 3H).

Workup

  1. customthe reaction was quenched with 10 mL of satd NH4Cl
  2. customThe organic layer was separated
  3. extractionthe aqueous layer was extracted with ether
  4. customdried
  5. concentrationconcentrated
  6. dissolutionThe residue was dissolved in 50 mL of methylene chloride
  7. temperaturethe solution was cooled to 0° C
  8. customthe reaction
  9. stirringmixtrue was stirred for 5 minutes
  10. customThe reaction was quenched with 1 N HCl (10 mL)
  11. customThe organic layer was separated
  12. extractionthe aqueous layer was extracted with methylene chloride
  13. customdried
  14. filtrationfiltered
  15. concentrationconcentrated

Sources & evidence

ORD record
ord-b68080b2a17c4815bce8181f3b0ccc79
Source dataset
uspto-grants-1997_01
Patent number
US05597832

Linked notes

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