Ethanolamine → HCID 12494252, compound

HRID 1195407Notes

Reaction equation

HRID 1195407 reaction equation
[CH3:1][Si:2]([CH3:15])([CH3:14])[C:3]#[C:4]B1C2CCCC1CCC2.[CH3:16][C:17]([CH3:21])([CH3:20])[CH:18]=[O:19].C(OCC)C.C(CN)O>CCCCC.CO>[CH3:16][C:17]([CH3:21])([CH3:20])[CH:18]([OH:19])[C:4]#[C:3][Si:2]([CH3:1])([CH3:14])[CH3:15]

Participants

7

Reactant 4

HCID 700EthanolamineHCID 3283Diethyl EtherHCID 12417PivalaldehydeHCID 10198312HCID 10198312, compound

Product 1

HCID 12494252HCID 12494252, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8003PentaneSolvent

Procedure

Dissolve B-(2-(trimethylsilyl)ethynyl)-9-borabicyclo[3.3.1]nonane.tetrahydrofuran complex (2.13 g, 7.3 mmol) in pentane (25 mL) and add trimethylacetaldehyde (795 μL, 7.3 mmol). Stir at room temperature for 5 days. Remove the solvent under a positive nitrogen pressure to give a yellow solid. Add ethyl ether (30 mL) and methanol (500 μL). Cool to 0° C. and add, by dropwise addition, ethanolamine (440 μL, 7.3 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 (1.25 g, 93%).

Workup

  1. customRemove the solvent under a positive nitrogen pressure
  2. customto give a yellow solid
  3. temperatureCool to 0° C.
  4. stirringStir overnight
  5. customcentrifuge the reaction mixture and separate the clear supernatant liquid
  6. washWash the precipitate with pentane (2×10 mL)
  7. washWash with water (2×25 mL)
  8. dry with materialdry (MgSO4)
  9. customEvaporate the solvent in vacuo
  10. custompurify by silica gel chromatography (19:1 hexane/ethyl acetate)

Sources & evidence

ORD record
ord-3c8f6dd18a40421381b1c5cd46cb26e3
Source dataset
uspto-grants-1992_05
Patent number
US05110966

Reaction notes

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