Iodoethane → HCID 9927970, compound

HRID 967958Notes

Reaction equation

HRID 967958 reaction equation
[Li][CH2:2][CH2:3][CH2:4][CH3:5].CCCCCC.BrC1[CH:33]=[C:32](C)[C:16]([O:17][C:18]2[C:23]([CH3:24])=[C:22]([O:25][CH:26]([CH2:29][CH3:30])[CH2:27][CH3:28])[CH:21]=[C:20]([CH3:31])[N:19]=2)=[C:15]([CH3:35])[CH:14]=1.C(I)C>C1COCC1>[CH2:4]([C:3]1[CH:2]=[C:32]([CH3:33])[C:16]([O:17][C:18]2[C:23]([CH3:24])=[C:22]([O:25][CH:26]([CH2:29][CH3:30])[CH2:27][CH3:28])[CH:21]=[C:20]([CH3:31])[N:19]=2)=[C:15]([CH3:35])[CH:14]=1)[CH3:5]

Participants

6

Reactant 4

HCID 6340IodoethaneHCID 8058HexaneHCID 9952426HCID 9952426, compoundHCID 178418339Butyllithium

Product 1

HCID 9927970HCID 9927970, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 2.5 N n-BuLi in hexane (0.47 ml, 1.18 mmol) in 5 ml of dry THF was added a solution of 2-(4-bromo-2,6-dimethyl-phenoxy)-4-(1-ethyl-propoxy)-3,6-dimethyl-pyridine (465 mg, 1.18 mmol) in 5 ml of dry THF at −78° C. After stirring at that temperature for 5 min, an excess of ethyl iodide (0.4 ml) was added and the resulting mixture was stirred at −78° C. for 30 min, then at 0° C. for 15 min. The mixture was quenched with saturated ammonium chloride and extracted with ethyl acetate. The organic layer was dried and concentrated to give a light brown oil. The oil was purified through silica gel column chromatography using chloroform as eluent to give 260 mg of the title compound as white solid. 1H NMR (CDCl3) δ 6.90 (s, 2H), 6.38 (s, 1H), 4.20 (m, 1H), 2.61 (q, 2H), 2.24 (s, 3H), 2.21 (s, 3H), 2.10 (s, 6H), 1.70 (m, 4H), 1.30 (t, 3H), 0.98 (t, 6H) ppm.

Workup

  1. stirringthe resulting mixture was stirred at −78° C. for 30 min
  2. waitat 0° C. for 15 min
  3. customThe mixture was quenched with saturated ammonium chloride
  4. extractionextracted with ethyl acetate
  5. customThe organic layer was dried
  6. concentrationconcentrated
  7. customto give a light brown oil
  8. customThe oil was purified through silica gel column chromatography

Sources & evidence

ORD record
ord-11854802616f4ac9966cc4dc0e7097bf
Source dataset
uspto-grants-2005_10
Patent number
US06956047B1

Reaction notes

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