Water → HCID 57733963, compound

HRID 469696Notes

Reaction equation

HRID 469696 reaction equation
I[C:2]1[CH:7]=[C:6](I)[C:5](I)=[CH:4][C:3]=1I.[CH2:11]([OH:16])[CH2:12][CH2:13][C:14]#[CH:15].[OH2:17]>CN(C=O)C.CCN(CC)CC.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>[C:2]1([C:15]#[C:14][CH2:13][CH2:12][CH2:11][OH:16])[CH:7]=[C:6]([C:15]#[C:14][CH2:13][CH2:12][CH2:11][OH:16])[C:5]([C:7]#[C:2][CH2:3][CH2:4][CH2:5][OH:17])=[CH:4][C:3]=1[C:15]#[C:14][CH2:13][CH2:12][CH2:11][OH:16]

Participants

7

Reactant 3

HCID 962WaterHCID 124881,2,4,5-TetraiodobenzeneHCID 793464-Pentyn-1-ol

Product 1

HCID 57733963HCID 57733963, compound

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 22056947triethylamine N,N-dimethylformamideSolvent

Procedure

To a degassed solution of 1,2,4,5-tetraiodobenzene (5.81 g, 0.01 mol) in DMF-Et3N (100 mL, 1:1) were added Pd(PPh3)2Cl2 (350 mg. 0.5 mmol), CuI (200 mg, 1.2 mmol), and 4-pentyn-1-ol (4.2 g, 0.05 mol) was added drop-wise. The mixture was stirred under N2 at room temperature for 24 h. The solution was poured into water (400 mL). The mixture was extracted with CH2Cl2 (3×200 mL). The combined organic phases were washed with 5% HCl and brine, dried over Na2SO4, and concentrated under vacuum. The residue was purified by silica gel column chromatography using CH2Cl2-MeOH (10:1, v/v) as eluent to afford tetramer (3.34 g, 82%): 1H NMR (300 MHz, CD3Cl+CO3OD δ ppm), 7.30 (s, 2H), 3.72 (t, J=6.3 Hz, 8H), 2.52 (t, J=7.2 Hz, 8H), 1.80 (p, J=6.6 Hz, 8H) ppm.

Workup

  1. additionwas added drop-wise
  2. extractionThe mixture was extracted with CH2Cl2 (3×200 mL)
  3. washThe combined organic phases were washed with 5% HCl and brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under vacuum
  6. customThe residue was purified by silica gel column chromatography
  7. customv/v) as eluent to afford tetramer (3.34 g, 82%)

Sources & evidence

ORD record
ord-e9198c8f91f8468f95de0a1f3576891b
Source dataset
uspto-grants-2014_01
Patent number
US08629163B2

Reaction notes

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