Pyridine → (Z)-8-Oxo-7,7-dimethyl-5-octenoic acid methyl ester

HRID 1388877Notes

Reaction equation

HRID 1388877 reaction equation
[CH3:1][O:2][C:3](=[O:14])[CH2:4][CH2:5][CH2:6]/[CH:7]=[CH:8]\[C:9]([CH3:13])([CH3:12])[CH2:10][OH:11].N1C=CC=CC=1>C(Cl)Cl>[CH3:1][O:2][C:3](=[O:14])[CH2:4][CH2:5][CH2:6]/[CH:7]=[CH:8]\[C:9]([CH3:12])([CH3:13])[CH:10]=[O:11]

Participants

4

Reactant 2

HCID 1049PyridineHCID 13276464(Z)-8-Hydroxy-7,7-dimethyl-5-octenoic acid methyl ester

Product 1

HCID 13276466(Z)-8-Oxo-7,7-dimethyl-5-octenoic acid methyl esterYield 77.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

0.530 g (2.65 mmoles) of (Z)-8-Hydroxy-7,7-dimethyl-5-octenoic acid methyl ester in 5 ml of methylene chloride was added slowly to a mixture of CrO3 (2.1 g; 21 mmol) and pyridine (3.5 g; 42 mmol) suspended in 55 ml of methylene chloride at room temperature. The reaction mixture was stirred for 5 hrs. The dichloromethane phase was decanted, and the precipitate was washed three times with ether. The organic phases were combined, washed with chilled 1 N sodium hydroxide, 1 N sulfuric acid, saturated sodium bicarbonate solution and brine then dried (MgSO4) and concentrated to give 0.53 g of crude material. Purification by chromatography or a silica gel column afforded 0.405 g (77.1%) of pure (Z)-8-Oxo-7,7-dimethyl-5-octenoic acid methyl ester (100% pure, by GC-analysis).

Workup

  1. customThe dichloromethane phase was decanted
  2. washthe precipitate was washed three times with ether
  3. washwashed
  4. temperaturewith chilled 1 N sodium hydroxide, 1 N sulfuric acid, saturated sodium bicarbonate solution and brine
  5. dry with materialthen dried (MgSO4)
  6. concentrationconcentrated
  7. customto give 0.53 g of crude material
  8. customPurification by chromatography

Sources & evidence

ORD record
ord-ba296ce63b64496c90ca8bdd438806f8
Source dataset
uspto-grants-1984_02
Patent number
US04434101

Reaction notes

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