Hydrochloric Acid → 7,7-Di-pyridin-2-yl-hept-6-enoic acid

HRID 404132Notes

Reaction equation

HRID 404132 reaction equation
[Li+].[OH-].C[O:4][C:5](=[O:24])[CH2:6][CH2:7][CH2:8][CH2:9][CH:10]=[C:11]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=1.Cl.CCOC(C)=O>O.C1COCC1>[N:13]1[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=1[C:11]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=1)=[CH:10][CH2:9][CH2:8][CH2:7][CH2:6][C:5]([OH:24])=[O:4]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 8857Ethyl AcetateHCID 585450277,7-Di-pyridin-2-yl-hept-6-enoic acid methyl ester

Product 1

HCID 585450627,7-Di-pyridin-2-yl-hept-6-enoic acidYield 47.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

LiOH (10 mg, 0.42 mmol) in water (0.2 mL) was added to III (25 mg, 0.085 mmol) in THF (0.8 mL) at rt. After 19 h, the reaction mixture was neutralized with 2N HCl, poured onto brine (2 mL), and EtOAc (3 mL) was added. The phases were separated and the aqueous phase was extracted with EtOAc (2×3 mL). The organic phases were combined, dried over MgSO4, filtered, and then evaporated under reduced pressure. The resulting residue was then purified by silica gel column chromatography using CH2Cl2/MeOH (100:2 to 100:4) as eluant to furnish IV as a colourless oil (11.3 mg, 46%).

Workup

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

Sources & evidence

ORD record
ord-ba3caa8bf0014fb49877379bd748ce7c
Source dataset
uspto-grants-2014_06
Patent number
US08748458B2

Reaction notes

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