Diethyl Ether → HCID 22908389, compound

HRID 1079013Notes

Reaction equation

HRID 1079013 reaction equation
[Si]([O:8][CH:9]1[CH2:13][C:12](=[CH2:14])[C:11]([CH:15]([CH3:18])[CH:16]=[CH2:17])=[CH:10]1)(C(C)(C)C)(C)C.CCOCC>O1CCCC1>[CH3:18][CH:15]([C:11]1[C:12](=[CH2:14])[CH2:13][CH:9]([OH:8])[CH:10]=1)[CH:16]=[CH2:17]

Participants

4

Reactant 2

HCID 3283Diethyl EtherHCID 22908410HCID 22908410, compound

Product 1

HCID 22908389HCID 22908389, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

2.02 Grams of (RS)-3-(1-methyl-2-propenyl)-4-methylidenecyclopent-2-en-1-yl t-butyldimethylsilyl ether was dissolved in 20 ml of tetrahydrofuran. Under ice-water cooling, 7.7 ml of a tetrahydrofuran solution of 1M n-tetrabutylammonium fluoride was added to the ether solution, and then stirred at an ambient temperature for six hours. The reaction solution was poured into ice-water and extracted with ether. The ether layer was washed with a saturated sodium chloride solution, and dried with anhydrous magnesium sulfate. After removal of the solvent under reduced pressure, the oily substance obtained was subjected to silica gel column chromatography to yield 1.05 g of (RS)-3-(1-methyl-2-propenyl)-4-methylidenecyclopent-2-en-1-ol.

Workup

  1. extractionextracted with ether
  2. washThe ether layer was washed with a saturated sodium chloride solution
  3. dry with materialdried with anhydrous magnesium sulfate
  4. customAfter removal of the solvent under reduced pressure
  5. customthe oily substance obtained

Sources & evidence

ORD record
ord-3927df5786aa475498c2c7364156a5b3
Source dataset
uspto-grants-1996_08
Patent number
US05550258

Reaction notes

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