Tetrahydrofuran → HCID 22449494, compound

HRID 2257829Notes

Reaction equation

HRID 2257829 reaction equation
C1C[O:4][CH2:3][CH2:2]1.CC(C)([O-])C.[K+].[C:12]([NH:15][C:16]1[CH:25]=[CH:24][C:23]([CH3:26])=[C:22]2[C:17]=1[C:18](=[O:27])[CH2:19][CH2:20][S:21]2)(=[O:14])[CH3:13].[N:28](OCCCC)=O>CCOCC>[C:3]([NH:28][CH:19]1[C:18](=[O:27])[C:17]2[C:22](=[C:23]([CH3:26])[CH:24]=[CH:25][C:16]=2[NH:15][C:12](=[O:14])[CH3:13])[S:21][CH2:20]1)(=[O:4])[CH3:2]

Participants

6

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 10996Butyl nitriteHCID 21828801HCID 21828801, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 22449494HCID 22449494, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To 3 ml of a THF solution containing 153 mg of potassium-t-butoxide was added 9 ml of a THF solution containing 291 mg of 5-acetylamino-8-methyl-4-thiochromanone [J. Heterocyclic Chem., 11, 515 (1974)]. After stirring for 5 minutes, 0.22 ml of n-butyl nitrite was added to the mixture, followed by further stirring for 1 hour at room temperature. After the addition of 20 ml of ether, the reaction mixture was stirred for another 1 hour. The deposited precipitate was collected by filtration, washed thoroughly with ether, and dissolved into a mixture of 20 ml of acetic acid and 20 ml of acetic anhydride. To the solution was added about 200 mg of zinc powder at room temperature while stirring. After the addition, the stirring was continued for a further 0.5 hour. Insoluble substances were removed by filtration, the solvent was evaporated, and 20 ml of chloroform was added to the residue. The residue, after washing with water, saturated aqueous solution of sodium hydroxide, and saturated brine in this order, was dried over anhydrous sodium sulfate. After evaporating the solvent, the residue was subjected to silica gel column chromatography using a hexane-ethyl acetate (4:1) mixed solvent as an eluant to obtain fractions containing the target compound. The fractions were concentrated to produce 109 mg of the title compound.

Workup

  1. stirringby further stirring for 1 hour at room temperature
  2. stirringthe reaction mixture was stirred for another 1 hour
  3. filtrationThe deposited precipitate was collected by filtration
  4. washwashed thoroughly with ether
  5. dissolutiondissolved into a mixture of 20 ml of acetic acid and 20 ml of acetic anhydride
  6. additionTo the solution was added about 200 mg of zinc powder at room temperature
  7. stirringwhile stirring
  8. additionAfter the addition
  9. waitthe stirring was continued for a further 0.5 hour
  10. customInsoluble substances were removed by filtration
  11. customthe solvent was evaporated
  12. addition20 ml of chloroform was added to the residue
  13. washThe residue, after washing with water, saturated aqueous solution of sodium hydroxide, and saturated brine in this order
  14. dry with materialwas dried over anhydrous sodium sulfate
  15. customAfter evaporating the solvent
  16. additionmixed solvent as an eluant
  17. customto obtain fractions
  18. additioncontaining the target compound
  19. concentrationThe fractions were concentrated

Sources & evidence

ORD record
ord-7d46e9cd28294df5a95a84689b03d8b9
Source dataset
uspto-grants-1997_08
Patent number
US05658920

Reaction notes

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