Tetrahydrofuran → HCID 86598850, compound

HRID 1592953Notes

Reaction equation

HRID 1592953 reaction equation
Cl[C:2]([O-:4])=[O:3].C[O:6][C:7]1[CH:12]=[CH:11][N:10]=[CH:9][CH:8]=1.[F:13][C:14]1[CH:19]=[CH:18][C:17]([Mg]Br)=[C:16]([CH3:22])[CH:15]=1.[CH2:23]1[CH2:27]O[CH2:25][CH2:24]1>>[F:13][C:14]1[CH:19]=[CH:18][C:17]([C@H:11]2[CH2:12][C:7](=[O:6])[CH:8]=[CH:9][N:10]2[C:2]([O:4][C@@H:23]2[CH2:27][C@H:14]([CH3:19])[CH2:15][CH2:25][C@H:24]2[CH:16]([CH3:22])[CH3:17])=[O:3])=[C:16]([CH3:22])[CH:15]=1

Participants

5

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 692784-MethoxypyridineHCID 21226386CarbonochloridateHCID 178427853HCID 178427853, compound

Product 1

HCID 86598850HCID 86598850, compound

Conditions

Temperature
-78 °C

Procedure

A solution of (−)-mentyl chloroformate (3.53 mL) in dry THF (15 mL) was added to a solution of 4-methoxypyridine (1.52 mL) in dry THF (35 mL) previously cooled to −78° C. under a nitrogen atmosphere. After 15 minutes, the solution containing the 4-fluoro-2-methyl-phenyl magnesium bromide was added drop-wise, and the mixture was stirred at −78° C. for 1 hour. The reaction was quenched by the addition of 1 M hydrochloric acid solution (20 mL), warmed to r.t. and stirred at 23° C. for 30 minutes. After extraction with AcOEt (2×150 mL), the combined organic extracts were washed with brine (50 mL), dried and concentrated in vacuo to a residue, which was purified by flash chromatography (CH/THF/toluene 8:1:1) to give:

Workup

  1. additionwas added drop-wise
  2. customThe reaction was quenched by the addition of 1 M hydrochloric acid solution (20 mL)
  3. temperaturewarmed to r.t.
  4. stirringstirred at 23° C. for 30 minutes
  5. extractionAfter extraction with AcOEt (2×150 mL)
  6. washthe combined organic extracts were washed with brine (50 mL)
  7. customdried
  8. concentrationconcentrated in vacuo to a residue, which
  9. customwas purified by flash chromatography (CH/THF/toluene 8:1:1)
  10. customto give

Sources & evidence

ORD record
ord-1c70210c007544f18bef4eaf59bcb28a
Source dataset
uspto-grants-2007_11
Patent number
US07294630B2

Reaction notes

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