Dimethylformamide → HCID 58892813, compound

HRID 545983Notes

Reaction equation

HRID 545983 reaction equation
[CH2:1]([C:11]1[S:15][C:14]([C:16]2[S:17][CH:18]=[CH:19][CH:20]=2)=[CH:13][CH:12]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].C([Li])CCC.CN([CH:29]=[O:30])C.[Cl-].[NH4+]>CCCCCC.C1COCC1>[CH2:1]([C:11]1[S:15][C:14]([C:16]2[S:17][C:18]([CH:29]=[O:30])=[CH:19][CH:20]=2)=[CH:13][CH:12]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 25517Ammonium ChlorideHCID 588928175-Decyl-2,2'-bithiopheneHCID 178418339Butyllithium

Product 1

HCID 58892813HCID 58892813, compoundYield 87.6%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Conditions

Temperature
0 °C

Procedure

5-Decyl-2,2′-bithiophene (39.0 g, 0.127 mol) prepared above and THF (300 ml) were placed in a 1000-ml three-necked flask equipped with a 200-ml dropping funnel and a reflux tube. The solution was cooled in an ice bath to 0° C., and a solution (80 ml) of n-butyllithium (1.6 M) in n-hexane was added dropwise to the cooled solution over a period of about one hr. After the completion of the dropwise addition, the mixture was stirred for about one hr. DMF (13.9 g, 0.191 mol) was added dropwise thereto at 0° C. over a period of about one hr. After the completion of the dropwise addition, the reaction temperature was raised to room temperature, and, at that temperature, the mixture was stirred overnight. After the completion of the reaction, a 1 N ammonium chloride solution (200 ml) was added, and the organic layer was extracted with diethyl ether, was dried over sodium sulfate, and was applied to column chromatography (CH2Cl2:hexane=1:1) to give an objective compound 5-decyl-5′-formyl-2,2′-bithiophene as a yellow solid (37.2 g, yield 87.60%). An NMR spectrum of the compound thus obtained was measured at room temperature with an NMR spectrometer (model JNM-LA400W, manufactured by Japan Electric Optical Laboratory). 1H-NMR (CDCl3, TMS/ppm): 0.88 (t, 3H, J=6.83 Hz), 1.26 (m, 14H), 1.69 (m, 2H), 2.81 (t, 2H, J=7.32 Hz), 6.74 (d, 1H, J=3.90 Hz), 7.16 (d, 1H, J=3.90 Hz), 7.18 (d, 1H, J=3.90 Hz), 7.64 (d, 1H, J=3.90 Hz), 9.84 (s, 1H).

Workup

  1. customwere placed in a 1000-ml three-necked flask
  2. customequipped with a 200-ml
  3. additionAfter the completion of the dropwise addition
  4. waitat 0° C. over a period of about one hr
  5. additionAfter the completion of the dropwise addition
  6. temperaturethe reaction temperature was raised to room temperature
  7. stirringat that temperature, the mixture was stirred overnight
  8. customAfter the completion of the reaction
  9. extractionthe organic layer was extracted with diethyl ether
  10. dry with materialwas dried over sodium sulfate

Sources & evidence

ORD record
ord-50020847c03c41e7a63393de56b1e976
Source dataset
uspto-grants-2011_05
Patent number
US07935828B2

Reaction notes

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