Tributyl(2-phenylethynyl)stannane → HCID 86601214, compound

HRID 349257

Reaction equation

HRID 349257 reaction equation
[CH2:1]([Sn:5]([CH2:18][CH2:19][CH2:20][CH3:21])([CH2:14][CH2:15][CH2:16][CH3:17])[C:6]#[C:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[CH2:2][CH2:3][CH3:4].[F:22][C:23]([F:39])([F:38])[C:24]1[CH:25]=[C:26]([CH:31]=[C:32]([C:34]([F:37])([F:36])[F:35])[CH:33]=1)[CH2:27][N:28]=[N+:29]=[N-:30]>C1(C)C=CC=CC=1>[F:22][C:23]([F:38])([F:39])[C:24]1[CH:25]=[C:26]([CH:31]=[C:32]([C:34]([F:37])([F:35])[F:36])[CH:33]=1)[CH2:27][N:28]1[C:7]([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)=[C:6]([Sn:5]([CH2:1][CH2:2][CH2:3][CH3:4])([CH2:14][CH2:15][CH2:16][CH3:17])[CH2:18][CH2:19][CH2:20][CH3:21])[N:30]=[N:29]1

Participants

4

Reactant 2

HCID 630640Tributyl(2-phenylethynyl)stannaneHCID 441857431-(Azidomethyl)-3,5-bis(trifluoromethyl)benzene

Product 1

HCID 86601214HCID 86601214, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Heat a mixture of tri-n-butyl-phenylethynyl-stannane (11.0 g, 30.0 mmol) and 3,5-bis-trifluoromethyl-benzyl azide (9.68 g, 36.0 mmol) in toluene (40 mL) at reflux until reaction is complete. Concentrate to remove the solvent in vacuo and purify the residue by flash chromatography on silica gel (elution with 17% ether in hexanes) to give the title compound (17.5 g, 26.4 mmol, 88%). MS (ES) 660.1, 662.1 (M+1); LC Rf=0.1 (17% ether in hexanes).

Workup

  1. temperatureHeat
  2. temperatureat reflux until reaction
  3. concentrationConcentrate
  4. customto remove the solvent in vacuo
  5. custompurify the residue by flash chromatography on silica gel (elution with 17% ether in hexanes)

Sources & evidence

ORD record
ord-69c4d2941ae84e44bf928c2351a234b2
Source dataset
uspto-grants-2007_02
Patent number
US07179804B2

Linked notes

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