Tetrabutylammonium Fluoride → (RS)-3-allyl-4-methyl-3-cyclopenten-1-ol

HRID 582742Notes

Reaction equation

HRID 582742 reaction equation
[Si]([O:8][CH:9]1[CH2:13][C:12]([CH3:14])=[C:11]([CH2:15][CH:16]=[CH2:17])[CH2:10]1)(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[CH2:15]([C:11]1[CH2:10][CH:9]([OH:8])[CH2:13][C:12]=1[CH3:14])[CH:16]=[CH2:17]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 57038877(RS)-3-allyl-4-methyl-3-cyclopenten-1-yl (t-butyldimethylsilyl) ether

Product 1

HCID 54075418(RS)-3-allyl-4-methyl-3-cyclopenten-1-olYield 53%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 2 g of (RS)-3-allyl-4-methyl-3-cyclopenten-1-yl (t-butyldimethylsilyl) ether in 20 g of tetrahydrofuran was added under ice-cooling 16 ml of 1 M tetrahydrofuran solution of tetrabutylammonium fluoride, and the resulting mixture was stirred at room temperature for 6 hours. Then the reaction liquid was poured into ice water and extracted with diethyl ether. The ether layer was washed with saturated aqueous sodium chloride solution, then dried over anhydrous magnesium sulfate and the solvent was distilled off under reduced pressure. The oily substance thus obtained was subjected to silica gel column chromatography to obtain 0.58 g of (RS)-3-allyl-4-methyl-3-cyclopenten-1-ol. Yield 53%

Workup

  1. customThen the reaction liquid
  2. extractionextracted with diethyl ether
  3. washThe ether layer was washed with saturated aqueous sodium chloride solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationthe solvent was distilled off under reduced pressure
  6. customThe oily substance thus obtained

Sources & evidence

ORD record
ord-9651da145d5d48508b25c16cbcbcaedd
Source dataset
uspto-grants-1999_07
Patent number
US05925676

Reaction notes

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