Dimethylformamide → HCID 14551988, compound

HRID 1432888Notes

Reaction equation

HRID 1432888 reaction equation
[Cl:1][C:2]1[S:6][C:5]([C:7]2[S:8][CH:9]=[CH:10][CH:11]=2)=[CH:4][CH:3]=1.[Li]CCCC.CN([CH:20]=[O:21])C>C1COCC1.CCOC(C)=O>[Cl:1][C:2]1[S:6][C:5]([C:7]2[S:8][C:9]([CH:20]=[O:21])=[CH:10][CH:11]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 6228DimethylformamideHCID 125014505-Chloro-2,2'-bithiopheneHCID 178418339Butyllithium

Product 1

HCID 14551988HCID 14551988, compoundYield 73.7%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 5-chloro-[2,2′]bithiophene (1.06 g, 5.28 mmol) in 12 mL of THF at −78° C. is added n-BuLi (4.4 mL of a 1.6M solution in hexanes, 6.99 mmol). After 15 minutes, DMF (0.97 mL, 14 mmol) is added and the resulting solution is allowed to warm to 0° C. After 15 min, the solution diluted with EtOAc and quenched with saturated NaHCO3 solution. The organic solution is washed with H2O and saturated NaCl solution, then dried over MgSO4, filtered and concentrated. The crude product is purified by flash column chromatography eluting with a gradient of 10% Et2O/hexanes to 20% Et2O/hexanes to yield the title compound (0.89 g, 3.89 mmol) as a white solid. 1H NMR (CDCl3, 300 MHz) δ9.87 (s, 1H), 7.70 (d, 1H), 7.20 (d, 1H), 7.15 (d, 1H), 6.91 (d, 1H).

Workup

  1. waitAfter 15 min
  2. customquenched with saturated NaHCO3 solution
  3. washThe organic solution is washed with H2O and saturated NaCl solution
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude product is purified by flash column chromatography
  8. washeluting with a gradient of 10% Et2O/hexanes to 20% Et2O/hexanes

Sources & evidence

ORD record
ord-1b5a0d8716e64da5b36ef841985871d4
Source dataset
uspto-grants-2009_11
Patent number
US07612075B2

Reaction notes

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