Hydrochloric Acid → HCID 86706803, compound

HRID 628233Notes

Reaction equation

HRID 628233 reaction equation
[Mg].C1C[O:5][CH2:4]C1.Br[C:8]1[S:9][CH:10]=[CH:11][C:12]=1[CH2:13][CH:14]([CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22].Cl>CN(C=O)C>[CH2:23]([CH:14]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[CH2:13][C:12]1[CH:11]=[CH:10][S:9][C:8]=1[CH:4]=[O:5])[CH2:24][CH2:25][CH2:26][CH2:27][CH3:28]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028Tetrahydrofuran3×HCID 5462224MagnesiumHCID 67453822HCID 67453822, compound

Product 1

HCID 86706803HCID 86706803, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

Magnesium (345 mg, 14.2 mmol) was added to a flask and put under a nitrogen atmosphere after sufficient deaeration. THF (10 ml) was added, and 2-bromo-3-(2-hexyldecyl)thiophene (A2) (5 g, 12.9 mmol) was dropped while refluxing THF. After the dropping, refluxing was similarly performed for three hours. THF (40 ml) was then added, and the flask was cooled to 0° C. DMF (10 ml) was dropped, and the temperature was increased to room temperature. The mixture was then stirred overnight. To the reaction solution, 1N hydrochloric acid (20 ml) was added, followed by extraction with chloroform. An organic layer was then washed with a saturated saline solution and water. The organic layer was dried with anhydrous magnesium sulfate, and, after filtration, the solvent 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 chloroform was used as a mobile phase, 3-(2-hexyldecyl)-2thiophenaldehyde (A3) was obtained as clear oil (3.0 g, 69% yield). The product (A3) obtained was identified using a 1H-NMR method. 1H-NMR (400 MHZ, CDCl3, TMS) δ 10.03 (s, 1 H), 7.64 (d, J=4.9 Hz, 1 H), 6.97 (d, J=4.9 Hz, 1 H), 2.88 (d, J=7.3 Hz, 2 H), 1.25 (m, 25 H), 0.88 (m, 6 H)

Workup

  1. temperatureAfter the dropping, refluxing
  2. temperaturethe temperature was increased to room temperature
  3. extractionfollowed by extraction with chloroform
  4. washAn organic layer was then washed with a saturated saline solution and water
  5. dry with materialThe organic layer was dried with anhydrous magnesium sulfate
  6. filtrationafter filtration
  7. distillationthe solvent was distilled off under reduced pressure
  8. customBy separating
  9. custompurifying
  10. customthe obtained reaction mixture by silica gel column chromatography in which a mixed solvent of hexane and chloroform

Sources & evidence

ORD record
ord-d84bb605cd0d4c669dd312c99c3620cd
Source dataset
uspto-grants-2016_04
Patent number
US09312491B2

Reaction notes

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