Water → 7,7-Di-pyridin-2-yl-hept-6-enoic acid methyl ester

HRID 404131Notes

Reaction equation

HRID 404131 reaction equation
[Br-].[PH4+].[N:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=1)=O.O.C[CH2:19][O:20][C:21]([CH3:23])=[O:22]>C1COCC1>[CH3:19][O:20][C:21](=[O:22])[CH2:23][CH2:9][CH2:4][CH2:5][CH:6]=[C:9]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=1)[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][N:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 88065Bis(2-pyridyl) ketoneHCID 21868956Phosphanium bromide

Product 1

HCID 585450277,7-Di-pyridin-2-yl-hept-6-enoic acid methyl esterYield 44%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

NHMDS (2.26 mL, 2.26 mmol) as a solution in THF was added to methyl 6-triphenylphosphonium bromide hexanoate II (1.072 g, 2.38 mmol) in THF (8 mL) at 0° C. under Ar(g). After 15 min, di-pyridin-2-yl-methanone (220 mg, 1.2 mmol) in THF (4 mL) was added; the reaction mixture was stirred for 1 h, and was then allowed to warm to rt. After 20 h stirring, water (15 mL) and EtOAc (15 mL) were added, the phases were separated, and the aqueous phase was extracted with EtOAc (2×10 mL). The organic phases were combined, dried over MgSO4, filtered, and then evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography using CH2Cl2/MeOH (100:0.5 to 100:2) as eluant to furnish III as a colourless oil (155 mg, 44%).

Workup

  1. stirringAfter 20 h stirring
  2. customthe phases were separated
  3. extractionthe aqueous phase was extracted with EtOAc (2×10 mL)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated under reduced pressure
  7. customThe resulting residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-54406ac0dbc942bfbe3724b186fb7213
Source dataset
uspto-grants-2014_06
Patent number
US08748458B2

Reaction notes

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