HCID 86742937, compound → HCID 70391585, compound

HRID 1722457Notes

Reaction equation

HRID 1722457 reaction equation
[CH2:1]([C:3]1([CH2:19][C:20]([O:22]C)=[O:21])[C:8]2[NH:9][C:10]3[C:15]([C:7]=2[CH2:6][CH2:5][O:4]1)=[CH:14][CH:13]=[CH:12][C:11]=3/[CH:16]=[CH:17]\[CH3:18])[CH3:2]>C(O)C.[OH-].[Na+]>[CH2:1]([C:3]1([CH2:19][C:20]([OH:22])=[O:21])[C:8]2[NH:9][C:10]3[C:15]([C:7]=2[CH2:6][CH2:5][O:4]1)=[CH:14][CH:13]=[CH:12][C:11]=3/[CH:16]=[CH:17]\[CH3:18])[CH3:2]

Participants

4

Reactant 1

HCID 86742937HCID 86742937, compound

Product 1

HCID 70391585HCID 70391585, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

(Z)-1-Ethyl-8-(1-propenyl)-1,3,4,9-tetrahydropyrano[3,4-b]indole-1-acetic acid, methyl ester (1.01 g, 3.2 mmol) was dissolved in a mixture of 11.2 mL of ethanol and 11.2 mL of 10% aqueous sodium hydroxide, and the solution was heated under reflux for 3 hours. The reaction mixture was then concentrated to dryness, and a mixture of 13.4 mL of ether and 13.4 mL of 10% aqueous sodium hydroxide was added to the residue. The layers were separated, and the aqueous layer was acidified with concentrated hydrochloric acid and extracted with ether (2×25 mL). The combined ether extracts were dried over anhydrous magnesium sulfate, filtered and concentrated to give 897 mg of the crude product. This material was purified by flash chromatography (20% ethyl acetate/hexane, H3PO4 treated silica gel) to give the desired product as a colorless oil which partially solidified upon standing. Trituration with petroleum ether provided 440 mg of an off-white solid, m.p. 89.5°-93.5° C.

Workup

  1. temperaturethe solution was heated
  2. temperatureunder reflux for 3 hours
  3. concentrationThe reaction mixture was then concentrated to dryness
  4. additiona mixture of 13.4 mL of ether and 13.4 mL of 10% aqueous sodium hydroxide
  5. additionwas added to the residue
  6. customThe layers were separated
  7. extractionextracted with ether (2×25 mL)
  8. dry with materialThe combined ether extracts were dried over anhydrous magnesium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customto give 897 mg of the crude product
  12. customThis material was purified by flash chromatography (20% ethyl acetate/hexane, H3PO4 treated silica gel)

Sources & evidence

ORD record
ord-9b846f05de1741a786064fcc229ea653
Source dataset
uspto-grants-1989_08
Patent number
US04855445

Reaction notes

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