Dimethylformamide → HCID 86706806, compound

HRID 628236Notes

Reaction equation

HRID 628236 reaction equation
P(Cl)(Cl)(Cl)=O.[CH2:6]([CH:10]([CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[CH2:11][O:12][C:13]1[CH:17]=[CH:16][S:15][CH:14]=1)[CH2:7][CH2:8][CH3:9].[OH-].[Na+].CN([CH:29]=[O:30])C>>[CH:29]([C:14]1[S:15][CH:16]=[CH:17][C:13]=1[O:12][CH2:11][CH:10]([CH2:6][CH2:7][CH2:8][CH3:9])[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])=[O:30]

Participants

5

Reactant 4

HCID 6228Dimethylformamide2×HCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 86706805HCID 86706805, compound

Product 1

HCID 86706806HCID 86706806, compoundYield 80%

Conditions

Temperature
70 °C

Procedure

Under a nitrogen atmosphere, phosphorous oxychloride (3.5 ml, 40 mmol) was slowly dropped into DMF (70 ml) at 0° C. and stirred for 10 minutes. Then, a DMF (15 ml) solution of 3-(2-butyloctoxy)thiophene (9 g, 30.4 mmol) was slowly dropped into the reaction solution. The reaction solution was then heated for two hours at 70° C. Then, the reaction solution was cooled to room temperature. While cooling the reaction solution in a water bath, a 10% aqueous sodium hydroxide solution was slowly added and stirred for 30 minutes. Then, the reaction solution was extracted with chloroform, and an organic layer was washed with a saturated saline solution and water. The organic layer was dried with anhydrous magnesium sulfate, and, after filtration, the solution was distilled off under reduced pressure. By separating and purifying the obtained reaction mixture by silica gel column chromatography in which a mixed solvent of hexane and ethyl acetate was used as a mobile phase, a target substance was obtained as clear oil (80% yield). 1H-NMR (400 MHZ, CDCl3, TMS) δ 10.00 (s, 1 H), 7.67 (d, J=4.8 Hz, 1 H), 6.84 (d, J=4.8 Hz, 1 H), 4.03 (d, J=4.8 Hz, 2 H), 1.25 (m, 17 H), 0.88 (m, 6 H)

Workup

  1. temperatureThen, the reaction solution was cooled to room temperature
  2. temperatureWhile cooling the reaction solution in a water bath
  3. stirringstirred for 30 minutes
  4. extractionThen, the reaction solution was extracted with chloroform
  5. washan organic layer was washed with a saturated saline solution and water
  6. dry with materialThe organic layer was dried with anhydrous magnesium sulfate
  7. filtrationafter filtration
  8. distillationthe solution was distilled off under reduced pressure
  9. customBy separating
  10. custompurifying
  11. customthe obtained reaction mixture by silica gel column chromatography in which a mixed solvent of hexane and ethyl acetate

Sources & evidence

ORD record
ord-2cb99499b48c44fe9edf3a2b1ffb6ad3
Source dataset
uspto-grants-2016_04
Patent number
US09312491B2

Reaction notes

Loading…