Triphenylphosphine → HCID 68408471, compound

HRID 1176175Notes

Reaction equation

HRID 1176175 reaction equation
I[C:2]1[CH:7]=[C:6]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])[C:5](I)=[CH:4][C:3]=1[O:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26].C1C=CC(P([C:40]2[CH:45]=CC=CC=2)C2C=CC=CC=2)=CC=1.[CH3:46][Si:47]([C:50]#[CH:51])([CH3:49])[CH3:48]>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.N1CCCCC1>[CH3:46][Si:47]([C:50]#[C:51][C:2]1[CH:7]=[C:6]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])[C:5]([C:40]#[C:45][Si:47]([CH3:49])([CH3:48])[CH3:46])=[CH:4][C:3]=1[O:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])([CH3:49])[CH3:48]

Participants

7

Reactant 3

HCID 11776TriphenylphosphineHCID 66111TrimethylsilylacetyleneHCID 113192531,4-Diiodo-2,5-bis(octyloxy)benzene

Product 1

HCID 68408471HCID 68408471, compound

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 8082PiperidineSolvent

Conditions

Temperature
60 °C

Procedure

1,4-Diiodo-2,5-di-n-octyloxybenzene (4.01 g, 6.84×10−3 mol), Pd(PPh3)2Cl2 (0.248 g, 3.53×10−4 mol), PPh3 (0.179 g, 6.82×10−4 mol), CuI (0.072 g, 3.8×10−4 mol) and piperidine (40 ml) were added to a 100-ml round-bottom flask. Ar was bubbled into the reaction mixture for 5 min before trimethylsilylacetylene (3.0 ml, 2.1×10−2 mol) was added. The reaction mixture was stirred at 60° C. for 2 h under Ar. After cooling, the solvent was evaporated. CHCl3 was added to the residue, and the organic solution was washed with aqueous NH4Cl (3 times), water, and dried over Na2SO4. After the solvent was evaporated, the residue was chromatographed on silica gel with 2:1 hexane:CHCl3 as the eluent. Yield=3.455 g (96% based on 4.01 g of 1,4-diiodo-2,5-di-n-octyloxybenzene). 1H NMR (300 MHz, CDCl3): δ 6.88 (s, 2H, Ph-H), 3.94 (t, 4H, J=6.4 Hz, —OCH2), 1.78 (quint, 4H, J=6.9 Hz, —OCH2CH2—), 1.42-1.60 (m, 4H, —OCH2CH2CH2—), 1.16-1.42 (m, 16H, —CH2—), 0.88 (t, 6H, J=6.7 Hz, —CH3), 0.25 (s, 18H, —Si—CH3). CI MS m/z: 526.366 (M+) (calcd 526.366).

Workup

  1. additionwas added
  2. temperatureAfter cooling
  3. customthe solvent was evaporated
  4. additionCHCl3 was added to the residue
  5. washthe organic solution was washed with aqueous NH4Cl (3 times), water
  6. dry with materialdried over Na2SO4
  7. customAfter the solvent was evaporated
  8. customthe residue was chromatographed on silica gel with 2:1 hexane

Sources & evidence

ORD record
ord-f874ca03d87f44269c09f5291c7f21eb
Source dataset
uspto-grants-2010_11
Patent number
US07842758B2

Reaction notes

Loading…