Hexane → HCID 22143613, compound

HRID 985246Notes

Reaction equation

HRID 985246 reaction equation
[Li]CCCC.CCCCCC.[Cl:12][C:13]1[CH:18]=[CH:17][N:16]=[C:15]2[CH:19]=[CH:20][S:21][C:14]=12.[C:22](Cl)(=[O:25])[CH2:23][CH3:24]>C1COCC1>[Cl:12][C:13]1[CH:18]=[CH:17][N:16]=[C:15]2[CH:19]=[C:20]([C:22](=[O:25])[CH2:23][CH3:24])[S:21][C:14]=12

Participants

6

Reactant 4

HCID 8058HexaneHCID 62324Propionyl chlorideHCID 112752517-Chlorothieno[3,2-b]pyridineHCID 178418339Butyllithium

Product 1

HCID 22143613HCID 22143613, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

2.5 M nBuLi in hexane (0.619 ml, 1.55 mmole) was added to a solution of 7-chlorothieno[3,2-b]pyridine (0.250 g, 1.47 mmole) in THF (5 ml) at −78° C. The reaction mixture was stirred at −78° C. for 30 min, and then propanoyl chloride (0.162 ml, 1.76 mmole) was added. The reaction mixture stirred at −78° C. and slowly warmed to 0° C. and quenched with H2O (10 ml), extracted with EtOAc (2×10 ml). The organic layer was dried over MgSO4 and concentrated. The residue was purified by flash column chromatography eluting with 10-70% EtOAc in hexane to a off-white solid (0.084 g, 25%). 1H NMR (300 MHz, CDCl3) δ8.66 (1H, d, J=4.9 Hz), 8.12 (1H, s), 7.38 (1H, d, J=4.9 Hz), 3.09 (2H, q, J=7.3 Hz), 1.29 (3H, t, J=7.3 Hz,); ESIMS (MH+): 225.95.

Workup

  1. stirringThe reaction mixture stirred at −78° C.
  2. temperatureslowly warmed to 0° C.
  3. customquenched with H2O (10 ml)
  4. extractionextracted with EtOAc (2×10 ml)
  5. dry with materialThe organic layer was dried over MgSO4
  6. concentrationconcentrated
  7. customThe residue was purified by flash column chromatography
  8. washeluting with 10-70% EtOAc in hexane to a off-white solid (0.084 g, 25%)

Sources & evidence

ORD record
ord-9b63e68e2a8c4bc393f9b718fac43544
Source dataset
uspto-grants-2005_03
Patent number
US06869962B2

Reaction notes

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