Tetrabutylammonium Fluoride → 1-Undecyn-3-ol

HRID 1073570Notes

Reaction equation

HRID 1073570 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 2x with diethyl ether. The combined ether extracts were washed 2x 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 6.81 g of the titled product as a yellow oil.

Workup

  1. temperatureThe reaction mixture became warm
  2. extractionextracted 2x with diethyl ether
  3. washThe combined ether extracts were washed 2x 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-b99ae7a80dbb40b9b2fe6ee9a10f6f68
Source dataset
uspto-grants-1990_11
Patent number
US04970229

Reaction notes

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