Tetrabutylammonium Fluoride → 1-Undecyn-3-ol

HRID 1073642Notes

Reaction equation

HRID 1073642 reaction equation
C[Si](C)(C)[C:3]#[C:4][CH:5]([OH:14])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13].[N+](CCCC)(CCCC)(CCCC)CCCC.[F-]>O1CCCC1.[Cl-].[Na+].O>[CH:3]#[C:4][CH:5]([OH:14])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13]

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 108900431-Undecyn-3-ol, 1-(trimethylsilyl)-

Product 1

HCID 2477661-Undecyn-3-olYield 112.5%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To 8.65 g of the crude product from Example 6 was added 40 ml of 1M (n-C4H9)4NF in tetrahydrofuran (THF). The reaction mixture became warm and stirring was continued at room temperature for 1/2 hour. Thereafter, the reaction mixture was poured into brine and extracted 2× with diethyl ether. The combined ether extracts were washed 2× with brine and then dried (MgSO4). Removal of the solvent produced a brown oil. The oil was flash chromatographed on a silica gel column. Gradient elution from 10% diethyl ether in petroleum ether to 20% diethyl ether in petroleum ether produced 6.81g of the titled product as a yellow oil.

Workup

  1. temperatureThe reaction mixture became warm
  2. extractionextracted 2× with diethyl ether
  3. washThe combined ether extracts were washed 2× with brine
  4. dry with materialdried (MgSO4)
  5. customRemoval of the solvent
  6. customproduced a brown oil
  7. customchromatographed on a silica gel column
  8. washGradient elution from 10% diethyl ether in petroleum ether to 20% diethyl ether in petroleum ether

Sources & evidence

ORD record
ord-eb082491ac8649e9a0451e3a92ba5cba
Source dataset
uspto-grants-1990_11
Patent number
US04970234

Reaction notes

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