Dichloromethane → HCID 57574460, compound

HRID 1092746Notes

Reaction equation

HRID 1092746 reaction equation
O=P(Cl)(Cl)Cl.[CH3:6][C:7]1([CH3:18])[C:17]2[CH:16]=[CH:15][S:14][C:13]=2[C:9]2[S:10][CH:11]=[CH:12][C:8]1=2.[C:19]([O-])([O-])=[O:20].[K+].[K+].C(Cl)Cl>C(Cl)Cl.CN(C=O)C>[CH3:6][C:7]1([CH3:18])[C:8]2[CH:12]=[C:11]([CH:19]=[O:20])[S:10][C:9]=2[C:13]2[S:14][CH:15]=[CH:16][C:17]1=2

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 11430Potassium CarbonateHCID 24813Phosphorus oxychlorideHCID 57574456HCID 57574456, compound

Product 1

HCID 57574460HCID 57574460, compound

Reagents, catalysts & solvents 1

HCID 22350042dichloromethane N,N-dimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

1 mL POCl3 was added to a vigorously stirred solution of 4,4-dimethyl-4H-cyclopenta[2,1-b:3,4-b′]dithiophene (381.2 mg, 1.85 mmol) in 6 mL 5:1 CH2Cl2/DMF solvent mixture. The mixture was sealed in a pressure vessel and stirred at 100° C. for 10 min. The solution turned yellow then red upon cooling down. The reaction mixture was then basified with K2CO3 solution, stirred for 30 min more at room temperature to allow complete hydrolysis. The organic product was then extracted with CH2Cl2, concentrated, and purified by column chromatography (SiO2, CH2Cl2) to furnish a yellow oil that solidifies on standing (204 mg, 47%). Rf (silica gel, CH2Cl2)=0.41; 1H NMR (400 MHz, CDCl3): δ 1.50 (s, 6 H, 2 CH3), 7.05 (d, J=4.8 Hz, 1 H, ArH), 7.40 (d, J=4.8 Hz, 1 H, ArH), 7.63 (s, 1 H, ArH), 9.83 (s, 1 H, CHO); MS (EI): m/z=234 [M]+.

Workup

  1. customThe mixture was sealed in a pressure vessel
  2. temperaturered upon cooling down
  3. stirringstirred for 30 min more at room temperature
  4. customhydrolysis
  5. extractionThe organic product was then extracted with CH2Cl2
  6. concentrationconcentrated
  7. custompurified by column chromatography (SiO2, CH2Cl2)
  8. customto furnish a yellow oil

Sources & evidence

ORD record
ord-2f772f06082443cda0c396f233d8becb
Source dataset
uspto-grants-2012_03
Patent number
US08129532B2

Reaction notes

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