4-Methylpyridine → HCID 22185485, compound

HRID 1768313Notes

Reaction equation

HRID 1768313 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([CH3:7])=[CH:3][CH:2]=1.C([N-]C(C)C)(C)C.[Li+].[Cl:16][C:17]1[CH:28]=[CH:27][C:20]([C:21](N(OC)C)=[O:22])=[CH:19][C:18]=1[O:29][CH3:30].[Cl-].[NH4+]>O1CCCC1>[Cl:16][C:17]1[CH:28]=[CH:27][C:20]([C:21](=[O:22])[CH2:7][C:4]2[CH:5]=[CH:6][N:1]=[CH:2][CH:3]=2)=[CH:19][C:18]=1[O:29][CH3:30]

Participants

6

Reactant 4

HCID 79634-MethylpyridineHCID 25517Ammonium ChlorideHCID 2724682Lithium diisopropylamideHCID 22185459HCID 22185459, compound

Product 1

HCID 22185485HCID 22185485, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

4-Picoline (16.9 ml, 0.174 mol) was added dropwise to a stirred solution of lithium di-isopropylamide (110 ml, 0.22 mol, 2M solution in heptane, ethylbenzene, tetrahydrofuran) in dry tetrahydrofuran (150 ml) at −78° C. After stirring at −78° C. for 15 minutes a solution of the product of Step 1 (40.0 g, 0.174 mol) in tetrahydrofuran (100 ml) was added dropwise. The reaction was allowed to warm to room temperature over 3 hours. The solution was cooled in ice and saturated ammonium chloride solution was added. The aqueous mixture was extracted with ethyl acetate, washed with brine, dried (MgSO4), filtered and concentrated at reduced pressure. The resulting gum was triturated with cold diethyl ether/hexane (1:1, 300 ml) and the solid collected to give the title compound, as a pale yellow solid (29 g, 64%); MS(ES+) m/e 262/264 [M+H]+.

Workup

  1. additionwas added dropwise
  2. temperatureThe solution was cooled in ice
  3. extractionThe aqueous mixture was extracted with ethyl acetate
  4. washwashed with brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated at reduced pressure
  8. customThe resulting gum was triturated with cold diethyl ether/hexane (1:1, 300 ml)
  9. customthe solid collected

Sources & evidence

ORD record
ord-11b42eda2f3346328de1f5d4753c5efb
Source dataset
uspto-grants-2007_06
Patent number
US07235658B2

Reaction notes

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