Pyridine → HCID 87843343, compound

HRID 2273831Notes

Reaction equation

HRID 2273831 reaction equation
[C:1](Cl)(=[O:5])[CH2:2][CH2:3][CH3:4].[C:7](=[C:10]([CH2:13][CH:14]=[C:15]([CH3:17])[CH3:16])[CH2:11][OH:12])([CH3:9])[CH3:8].N1C=CC=CC=1.C(=O)(O)[O-].[Na+]>C(#N)C>[C:1]([O:12][CH2:11][C:10](=[C:7]([CH3:9])[CH3:8])[CH2:13][CH:14]=[C:15]([CH3:17])[CH3:16])(=[O:5])[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 4

HCID 1049PyridineHCID 8855Butyryl chlorideHCID 516892Sodium BicarbonateHCID 123110785-Methyl-2-(1-methylethylidene)-4-hexen-1-ol

Product 1

HCID 87843343HCID 87843343, compoundYield 97.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

In a nitrogen atmosphere, 64.0 g of butyryl chloride was added dropwise to a mixture of 94.1 g of 2-isopropylidene-5-methyl-4-hexenol (3) having a purity of 81.1% and an α,β-isomer purity of 98.1%, 50 g of pyridine and 500 ml of acetonitrile over 55 minutes which was stirred under cooling with ice. The reaction mixture was stirred for 2 hours under cooling with ice. To the reaction mixture was added an aqueous solution of saturated sodium bicarbonate, followed by extraction with diethyl ether. The diethyl ether solution was subjected to work-up including washing, drying and concentration to obtain 131.22 g of the crude product. The crude product was purified by distillation under reduced pressure to obtain, as the intended product, 23.54 g of a fraction having a purity of 92.8% and an α,β-isomer purity of 97.0% and 82.05 g of a fraction having a purity of 92.2% and an α,β-isomer purity of 98.3%. The yield of fractions including the other fractions was 95%.

Workup

  1. temperatureunder cooling with ice
  2. temperatureunder cooling with ice
  3. extractionfollowed by extraction with diethyl ether
  4. washto work-up including washing
  5. customdrying
  6. concentrationconcentration

Sources & evidence

ORD record
ord-eb88c11bdd3d42059bd91412c89b09fe
Source dataset
uspto-grants-2015_09
Patent number
US09126920B2

Reaction notes

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