HCID 13037851, compound → HCID 22908389, compound

HRID 1079012Notes

Reaction equation

HRID 1079012 reaction equation
[Br-].C1([C:8]([PH3+])([C:15]2[CH:20]=CC=[CH:17][CH:16]=2)[C:9]2[CH:14]=[CH:13][CH:12]=C[CH:10]=2)C=CC=CC=1.CC(C)([O-:25])C.[K+].CC(C1C(=O)CC(O)C=1)C=C.P([O-])(O)(O)=O.[Na+]>CCOCC.C(O)(C)(C)C>[CH3:20][CH:15]([C:8]1[C:9](=[CH2:10])[CH2:14][CH:13]([OH:25])[CH:12]=1)[CH:16]=[CH2:17]

Participants

7

Reactant 4

HCID 13037851HCID 13037851, compoundHCID 21951224Triphenylmethyl phosphonium bromideHCID 23665647Potassium tert-butoxideHCID 23672064Monosodium phosphate

Product 1

HCID 22908389HCID 22908389, compoundYield 12.4%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 6386tert-ButanolSolvent

Procedure

A mixture of 12.5 ml of ether, 1.0 ml of t-butanol and 3.85 g of triphenylmethylphosphonium bromide was stirred at an ambient temperature, then 1.21 g of potassium t-butoxide was added to the mixture and stirred at an ambient temperature for five hours. Under ice-water cooling, 1.64 g of (RS)-3-(1-methyl-2-propenyl)4-oxocyclopent-2-en-1-ol dissolved in 2.0 ml of ether was added dropwise to the mixed solution and stirred for two hours. The mixture was subsequently stirred at an ambient temperature for six hours. The reaction solution was poured into a saturated aqueous sodium dihydrogen phosphate solution and extracted with ether. The organic layer was 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 0.20 g of (RS)-3-(1-methyl-2-propenyl)-4-methylidene-cyclopent-2-en-1-ol. Yield 12%

Workup

  1. stirringstirred at an ambient temperature for five hours
  2. additionwas added dropwise to the mixed solution
  3. stirringstirred for two hours
  4. stirringThe mixture was subsequently stirred at an ambient temperature for six hours
  5. extractionextracted with ether
  6. washThe organic layer was washed with a saturated sodium chloride solution
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customAfter removal of the solvent under reduced pressure

Sources & evidence

ORD record
ord-e8590fa68abb49ffa388670b1cfac83a
Source dataset
uspto-grants-1996_08
Patent number
US05550258

Reaction notes

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