Pyridine → HCID 22908396, compound

HRID 1379935Notes

Reaction equation

HRID 1379935 reaction equation
CC(C1C(=C)CC([OH:11])C=1)C=C.N1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[CH3:18][C:19]1([CH3:27])[C:21]([CH3:23])([CH3:22])[CH:20]1[C:24](Cl)=[O:25].[C:28]1([CH3:34])[CH:33]=[CH:32]C=C[CH:29]=1>>[CH3:18][C:19]1([CH3:27])[C:21]([CH3:23])([CH3:22])[CH:20]1[C:24]([O:11][C:13]1[CH:29]([CH:28]([CH3:34])[CH:33]=[CH2:32])[C:16](=[CH2:17])[CH2:15][CH:14]=1)=[O:25]

Participants

5

Reactant 4

HCID 1049PyridineHCID 1140Toluene3×HCID 110410022,2,3,3-Tetramethylcyclopropane-1-carbonyl chlorideHCID 22908389HCID 22908389, compound

Product 1

HCID 22908396HCID 22908396, compoundYield 62%

Procedure

After 0.21 g of (RS)-3-(1-methyl-2-propenyl)-4-methylidenecyclopent-2-en-1-ol was dissolved in 5 ml of toluene, 0.14 ml of pyridine was added to the toluene solution. Under ice-water cooling, 70%(w/w) toluene solution containing 0.32 g of 2,2,3,3-tetramethylcyclopropanecarboxylic acid chloride was added dropwise to the mixed solution, and then stirred at an ambient temperature for six hours. The reaction solution was poured into ice-water and extracted with ethyl acetate. The ethyl acetate layer was washed successively with 5% aqueous hydrochloric acid and water, and vigorously stirred with 5% ammonia water for two hours. The ethyl acetate layer was then washed with a saturated sodium chloride solution and dried over anhydrous magnesium sulfate. After removal of the solvent under reduced pressure, the obtained oily substance was subjected to silica gel column chromatography to yield 0.24 g of (RS)-3-(1-methyl-2-propenyl)-4-methylidenecyclopenten-2-yl 2,2,3,3-tetramethylcyclopropanecarboxylate (Compound No.12). Yield 62% nD23 1.5023

Workup

  1. additionwas added dropwise to the mixed solution
  2. extractionextracted with ethyl acetate
  3. washThe ethyl acetate layer was washed successively with 5% aqueous hydrochloric acid and water
  4. stirringvigorously stirred with 5% ammonia water for two hours
  5. washThe ethyl acetate layer was then washed with a saturated sodium chloride solution
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customAfter removal of the solvent under reduced pressure

Sources & evidence

ORD record
ord-62f21a72bdb0423a9e7068b180d0c8ad
Source dataset
uspto-grants-1997_09
Patent number
US05672779

Reaction notes

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