Trimethylsilylacetylene → HCID 12079586, compound

HRID 1176166Notes

Reaction equation

I[C:2]1[CH:20]=[CH:19][C:5]([N:6]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])=[CH:4][CH:3]=1.[CH3:21][Si:22]([C:25]#[CH:26])([CH3:24])[CH3:23]>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu]I.CCN(CC)CC>[CH3:21][Si:22]([C:25]#[C:26][C:2]1[CH:20]=[CH:19][C:5]([N:6]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])=[CH:4][CH:3]=1)([CH3:24])[CH3:23]

Participants

Conditions

Temperature: 45 °C

Procedure

4-Iodo-N,N-dihexylaniline (3.150 g, 8.13×10−3 mol), Pd(PPh3)2Cl2 (0.332 g, 4.73×10−4 mol), CuI (0.130 g, 6.83×10−4 mol) and Et3N (20 ml) were added to a 100-ml round-bottom flask. Ar was bubbled into the reaction mixture for 5 min before (trimethylsilyl)acetylene (2.40 ml, 1.70×10−2 mol) was added. The reaction mixture was stirred at 45° C. for 18 h under Ar. After the solvent was removed in vacuo, the residue was chromatographed on silica gel 4:1 hexane:CHCl3 as the eluent. Yield=2.861 g (98% based on 3.150 g of 4-iodo-N,N-dihexylaniline). 1H NMR (250 MHz, CDCl3): δ 7.29 (d, 2H, J=9.0 Hz, Ph), 6.50 (d, 2H, J=9.0 Hz, Ph), 3.24 (t, 4H, J=7.7 Hz, —NCH2—), 1.43-1.65 (m, 4H, —NCH2CH2—), 1.19-1.41 (m, 12H, —CH3—), 0.89 (t, 6H, J=6.5 Hz, —CH3), 0.22 (s, 9H, Si—CH3). CI MS m/z: 358.292 ((M+H)+) (calcd 358.293).

Workup

additionwas added
customAfter the solvent was removed in vacuo
customthe residue was chromatographed on silica gel 4:1 hexane

Sources & evidence

ORD record: ord-36fd23d21a7546db963c748a0d7cb061
Source dataset: uspto-grants-2010_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07842758B2

Reaction notes

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