Tetrabutylammonium Fluoride → HCID 12952598, compound

HRID 1079001Notes

Reaction equation

HRID 1079001 reaction equation
[CH3:1][C:2]1[C:3]([O:17][SiH3])(C(C)(C)C)[C:4](C)(C)[C:5](=[CH2:10])[C:6]=1[CH2:7][CH:8]=[CH2:9].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[CH3:1][C:2]1[CH:3]([OH:17])[CH2:4][C:5](=[CH2:10])[C:6]=1[CH2:7][CH:8]=[CH2:9]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 131719507HCID 131719507, compound

Product 1

HCID 12952598HCID 12952598, compoundYield 82.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

3 To a solution of (RS)-2-methyl-4-methylidene-3-(2-propenyl)-1-tert-butyldimethyl-silyloxycyclopent-2-ene (1.0 g, obtained above) in dry tetrahydrofuran (10 ml) was added a tetrahydrofuran solution (5.7 ml) of 1M tetrabutylammonium fluoride under ice-water cooling. The solution was then stirred at room temperature for 12 hours. The reaction solution was poured into ice-water, and extracted with ether (100 ml×2). The ether layers were combined and washed with brine, and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The resultant residue was subjected to silica gel column chromatography (eluent; n-hexane: ethyl acetate=3:1) to afford the desired product (RS)-2-methyl-4-methylidene3-(2-propenyl)cyclopent-2-ene-1-ol (460 mg, yield 82.3%) as a pale yellow oil.

Workup

  1. extractionextracted with ether (100 ml×2)
  2. washwashed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-3e09ff946cff4a3cb037521bb0a79e95
Source dataset
uspto-grants-1996_08
Patent number
US05550260

Reaction notes

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