Triethylamine → 10-(4-Tributylstannyl-[1,2,3]triazol-1-yl)-decanoic acid

HRID 2280233Notes

Reaction equation

HRID 2280233 reaction equation
[N:1]([CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]([OH:15])=[O:14])=[N+:2]=[N-:3].[CH2:16]([Sn:20]([C:29]#[CH:30])([CH2:25][CH2:26][CH2:27][CH3:28])[CH2:21][CH2:22][CH2:23][CH3:24])[CH2:17][CH2:18][CH3:19].C(N(CC)CC)C>C1COCC1>[CH2:25]([Sn:20]([CH2:21][CH2:22][CH2:23][CH3:24])([CH2:16][CH2:17][CH2:18][CH3:19])[C:29]1[N:3]=[N:2][N:1]([CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]([OH:15])=[O:14])[CH:30]=1)[CH2:26][CH2:27][CH3:28]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 621176EthynyltributyltinHCID 8571414410-Azidodecanoic acid

Product 1

HCID 6797543910-(4-Tributylstannyl-[1,2,3]triazol-1-yl)-decanoic acidYield 8.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

10-Azidodecanoic acid (2.0 g, 9.5 mmol) in THF (50 mL) is treated with tributylstannyl acetylene (2.99 g, 9.5 mmol) copper(I)iodide (90 mg 0.47 mmol) and triethylamine (256 mg, 2.54 mmol) at room temperature with constant stirring for 24 h. The reaction is then filtered through celite and concentrated in vacuo to a gum, and then chromatographed on silica in a gradient of 10-40% ethyl acetate in petrol. The main fraction is collected and concentrated in vacuo to give 10-(4-tributylstannyl-[1,2,3]triazol-1-yl)-decanoic acid (3.22 g, 0.8 mmol).

Workup

  1. filtrationThe reaction is then filtered through celite and
  2. concentrationconcentrated in vacuo to a gum
  3. customchromatographed on silica in a gradient of 10-40% ethyl acetate in petrol
  4. customThe main fraction is collected
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-bf7f7baeab5f48099737ec8d94884ba9
Source dataset
uspto-grants-2015_09
Patent number
US09138493B2

Reaction notes

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