Dimethylformamide → HCID 23117348, compound

HRID 131649Notes

Reaction equation

HRID 131649 reaction equation
[CH2:1](I)[CH2:2][CH2:3][CH3:4].C(=O)([O-])[O-].[K+].[K+].CN(C)C=O.[C:17]([C:20]1[S:24][C:23]2[C:25]3[C:30]([CH2:31][CH2:32][C:22]=2[CH:21]=1)=[CH:29][C:28]([OH:33])=[CH:27][CH:26]=3)(=[O:19])[CH3:18]>C(OCC)(=O)C.CCCCCC.O>[C:17]([C:20]1[S:24][C:23]2[C:25]3[C:30]([CH2:31][CH2:32][C:22]=2[CH:21]=1)=[CH:29][C:28]([O:33][CH2:1][CH2:2][CH2:3][CH3:4])=[CH:27][CH:26]=3)(=[O:19])[CH3:18]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 10962Butyl iodideHCID 11430Potassium CarbonateHCID 23117349HCID 23117349, compound

Product 1

HCID 23117348HCID 23117348, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21226206Ethyl acetate hexaneSolvent

Conditions

Temperature
80 °C

Procedure

0.46 mL of butyl iodide and 0.83 g of potassium carbonate were added to a 10 mL dimethylformamide solution of 0.5 g of the compound obtained in Example 39, and the system was stirred for 2 hours at 80° C. After the reaction, water was added and extraction was performed with ethyl acetate. The extracted organic layer was washed with saturated brine, dried with magnesium sulfate, and then subjected to reduced-pressure solvent distillation. The residue thus obtained was refined by silica gel column chromatography (10% ethyl acetate/hexane) and then recrystallized with ethanol to obtain 0.48 g of 2-acetyl-4,5-dihydro-7-(n-butyloxy)naphtho[1,2-b]thiophene (Table 7-1) in the form of yellow crystals.

Workup

  1. additionwas added
  2. extractionextraction
  3. washThe extracted organic layer was washed with saturated brine
  4. dry with materialdried with magnesium sulfate
  5. distillationsubjected to reduced-pressure solvent distillation
  6. customThe residue thus obtained
  7. customrecrystallized with ethanol

Sources & evidence

ORD record
ord-965826e33f8d4e918402e21fc4f430c3
Source dataset
uspto-grants-2008_06
Patent number
US07384974B2

Reaction notes

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