Propanal → HCID 67336197, compound

HRID 1671320Notes

Reaction equation

HRID 1671320 reaction equation
C([Mg]Cl)(C)C.[Li]CCCC.Br[C:12]1[C:13]([CH3:20])=[CH:14][C:15]([O:18][CH3:19])=[N:16][CH:17]=1.[CH:21](=[O:24])[CH2:22][CH3:23]>C1COCC1>[CH3:19][O:18][C:15]1[N:16]=[CH:17][C:12]([CH:21]([OH:24])[CH2:22][CH3:23])=[C:13]([CH3:20])[CH:14]=1

Participants

6

Reactant 4

HCID 527PropanalHCID 41780025-Bromo-2-methoxy-4-methylpyridineHCID 178418339ButyllithiumHCID 178418918HCID 178418918, compound

Product 1

HCID 67336197HCID 67336197, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a cooled (−10° C.) solution of iPrMgCl (2.0M in THF, 619 ul, 1.24 mmol, 0.5 eq) in THF (5 ml) at is added n-BuLi (2.5M in hexanes, 990 ul, 2.47 mmol, 1 eq) and the mixture stirred at this temperature for 15 mins. This mixture is treated with a solution of 5-bromo-2-methoxy-4-methyl-pyridine (500 mg, 2.47 mmol) in THF (5 ml) and allowed to stir at −10° C. for 30 mins. After this time, propionaldehyde (0.324 ml, 4.45 mmol, 1.8 eq) is added and the contents left stirring for 2 hrs. The reaction is quenched with acetic acid (500 ul). The mixture is partitioned between EtOAc (100 ml) and Na2CO3 (2M, 50 ml) and the organic layer is separated, washed successively with 2M Na2CO3, water and brine, dried over MgSO4, filtered, and evaporated to yield the title compound as a clear oil. The crude 1-(6-methoxy-4-methyl-pyridin-3-yl)-propan-1-ol is used without further purification. MS: m/z 182.1 [M+H]+.

Workup

  1. stirringto stir at −10° C. for 30 mins
  2. waitthe contents left
  3. stirringstirring for 2 hrs
  4. customThe reaction is quenched with acetic acid (500 ul)
  5. customThe mixture is partitioned between EtOAc (100 ml) and Na2CO3 (2M, 50 ml)
  6. customthe organic layer is separated
  7. washwashed successively with 2M Na2CO3, water and brine
  8. dry with materialdried over MgSO4
  9. filtrationfiltered
  10. customevaporated

Sources & evidence

ORD record
ord-8b23b402cfd94f79b2813c549a5a2476
Source dataset
uspto-grants-2011_08
Patent number
US07994203B2

Reaction notes

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