Ethynyltributyltin → 3-[4-(tributylstannanyl)-1H-1,2,3-triazol-1-yl]propan-1-ol

HRID 2279897Notes

Reaction equation

[CH2:1]([Sn:5]([C:14]#[CH:15])([CH2:10][CH2:11][CH2:12][CH3:13])[CH2:6][CH2:7][CH2:8][CH3:9])[CH2:2][CH2:3][CH3:4].[N:16]([CH2:19][CH2:20][CH2:21][OH:22])=[N+:17]=[N-:18]>C1(C)C=CC=CC=1>[CH2:10]([Sn:5]([CH2:6][CH2:7][CH2:8][CH3:9])([CH2:1][CH2:2][CH2:3][CH3:4])[C:14]1[N:18]=[N:17][N:16]([CH2:19][CH2:20][CH2:21][OH:22])[CH:15]=1)[CH2:11][CH2:12][CH3:13]

Participants

Conditions

Temperature: 110 °C

Procedure

A solution of tributylstannylethyne (1.47 g, 4.67 mmol) and 3-azidopropan-1-ol (450 mg, 4.4 mmol) in PhMe (15 mL) was heated at 80° C. under nitrogen for 3 days. Another 0.5 eq. of Tributylstannylethyne was added, and the resulting mixture was heated at 110° C. for 5 h. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel chromatography (ISCO system: acetone/heptane=0-30%) to give the desired product as a colorless oil, 1.42 g, 77% yield. 1H NMR (CDCl3, 400 MHz): δ=7.48 (s, 1H), 4.57 (d, J=6.6 Hz, 2H), 3.63-3.67 (m, 2H), 2.11-2.17 (m, 2H), 1.95 (br s, 1H), 1.54-1.58 (m, 6H), 1.33-1.37 (m, 6H), 1.10-1.14 (m, 6H), 0.89 (t, J=7.3 Hz, 9H).

Workup

customThe solvent was evaporated under reduced pressure
customthe residue was purified by silica gel chromatography (ISCO system: acetone/heptane=0-30%)

Sources & evidence

ORD record: ord-b4fdd52cb7f8474ea1e7ed9c1b466a21
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09133224B2

Reaction notes

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