Hydrochloric Acid → HCID 13603323, compound

HRID 2309389Notes

Reaction equation

HRID 2309389 reaction equation
[H-].[Na+].[CH3:3][C:4]1([CH3:19])[O:18][C:7]2=[CH:8][C:9]3[CH2:10][C:11](=[O:17])[N:12]([CH2:15][CH3:16])[C:13]=3[CH:14]=[C:6]2[CH2:5]1.[C:20](=O)([O:24]CC)[O:21][CH2:22][CH3:23].Cl>C(Cl)Cl.C1C=CC=CC=1>[CH3:19][C:4]1([CH3:3])[O:18][C:7]2=[CH:8][C:9]3[CH:10]([C:20]([O:21][CH2:22][CH3:23])=[O:24])[C:11](=[O:17])[N:12]([CH2:15][CH3:16])[C:13]=3[CH:14]=[C:6]2[CH2:5]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7766Diethyl CarbonateHCID 24758Sodium hydrideHCID 20185151HCID 20185151, compound

Product 1

HCID 13603323HCID 13603323, compoundYield 51%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 6344DichloromethaneSolvent

Procedure

To a slurry of 26.4 mg. (1.1 mmoles) of sodium hydride in 2 ml. of benzene was added 231 mg. (1 mmole) of 2,2-dimethyl-5-ethyl-6-oxo-2,3,6,7-tetrahydro-furo[2,3-f]indole and the resultant reaction mixture stirred for 5 minutes. To the reaction mixture was added 0.13 ml. (1.1 mmoles) of diethyl carbonate, and the mixture allowed to stir 18 hours. The reaction is then added to methylene chloride and 4N hydrochloric acid, and the organic phase separated, washed with water and a saturated brine solution and dried over magnesium sulfate. The extract was subsequently treated with 1N sodium hydroxide solution and the basic layer separated. The aqueous basic layer was acidified and the product extracted with methylene chloride. The organic phase was separated, dried with magnesium sulfate and concentrated to give 155 mg. (51% yield) of the titled intermediate as an oil.

Workup

  1. additionTo the reaction mixture was added 0.13 ml
  2. stirringto stir 18 hours
  3. customthe organic phase separated
  4. washwashed with water
  5. dry with materiala saturated brine solution and dried over magnesium sulfate
  6. additionThe extract was subsequently treated with 1N sodium hydroxide solution
  7. customthe basic layer separated
  8. extractionthe product extracted with methylene chloride
  9. customThe organic phase was separated
  10. dry with materialdried with magnesium sulfate
  11. concentrationconcentrated
  12. customto give 155 mg

Sources & evidence

ORD record
ord-8c4a18ccd46b415893bb517090e53c6f
Source dataset
uspto-grants-1987_09
Patent number
US04695571

Reaction notes

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