Ethanolamine → 1-Decyn-3-ol, 1-(trimethylsilyl)-

HRID 1195405Notes

Reaction equation

HRID 1195405 reaction equation
[CH3:1][Si:2]([CH3:15])([CH3:14])[C:3]#[C:4]B1C2CCCC1CCC2.C([O:18][CH2:19][CH3:20])C.CO.[CH2:23]([CH2:25]N)O.[CH3:27][CH2:28][CH2:29][CH2:30]C>>[CH3:1][Si:2]([CH3:14])([CH3:15])[C:3]#[C:4][CH:19]([OH:18])[CH2:20][CH2:27][CH2:28][CH2:29][CH2:30][CH2:23][CH3:25]

Participants

6

Reactant 5

HCID 700EthanolamineHCID 887MethanolHCID 3283Diethyl EtherHCID 8003PentaneHCID 10198312HCID 10198312, compound

Product 1

HCID 109552841-Decyn-3-ol, 1-(trimethylsilyl)-Yield 91%

Procedure

Dissolve B-(2-(trimethylsilyl)ethynyl)-9-borabicyclo[3.3.1]nonane.tetrahydrofuran complex (2.4 g, 8.3 mmol) in pentane (25 mL) and add octylaldehyde (1.3 mL, 8.3 mmol). Stir at room temperature for 40 minutes and evaporate the solvent under a positive pressure of nitrogen to give a yellow solid. Add ethyl ether (30 mL) and methanol (336 μL, 8.3 mmol), cool to 0° C. and add, by dropwise addition, ethanolamine (0.5 mL, 8.3 mmol). Stir overnight, centrifuge the reaction mixture and separate the clear supernatant liquid. Wash the precipitate with pentane (2×10 mL) and combine the organic phases. Wash with water (2×25 mL) and dry (MgSO4). Evaporate the solvent in vacuo and purify by silica gel chromatography (19:1 hexane/ethyl acetate) to give the title compound as a clear liquid (1.71 g, 91%).

Workup

  1. customevaporate the solvent under a positive pressure of nitrogen
  2. customto give a yellow solid
  3. stirringStir overnight
  4. customcentrifuge the reaction mixture and separate the clear supernatant liquid
  5. washWash the precipitate with pentane (2×10 mL)
  6. washWash with water (2×25 mL)
  7. dry with materialdry (MgSO4)
  8. customEvaporate the solvent in vacuo
  9. custompurify by silica gel chromatography (19:1 hexane/ethyl acetate)

Sources & evidence

ORD record
ord-50626ebc43a749bba3db7eb5145d2a4d
Source dataset
uspto-grants-1992_05
Patent number
US05110966

Reaction notes

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