HCID 67060813, compound → HCID 67060779, compound

HRID 410011Notes

Reaction equation

HRID 410011 reaction equation
[CH2:1]([C:7]1[O:8][C:9](I)=[CH:10][CH:11]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]>C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:1]([C:7]1[O:8][C:9]([C:7]2[O:8][CH:9]=[CH:10][CH:11]=2)=[CH:10][CH:11]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

4

Reactant 1

HCID 67060813HCID 67060813, compound

Product 1

HCID 67060779HCID 67060779, compoundYield 174.1%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Procedure

Pd(PPh3)4 (1.15 g, 1 mmol, 5% mol) was added to 2-tributyltinfuran (7.05 g, 20 mmol) and 2-hexyl-5-iodofuran (5.5 g, 20 mmol) in dry toluene (150 mL) and the reaction mixture was refluxed under N2 for 5 h. The mixture was then cooled, separated with hexane, the organic layer was dried over MgSO4, filtered, and concentrated. The crude product was purified by silica gel column chromatography (elution with hexane) to afford 3.8 g of 5-hexyl-2,2′-bifuran (88%) as a colorless oil. 1H NMR (300 MHz, CDCl3): δ 7.35 (d, J=1.1 Hz, 1H), 6.39-6.45 (m, 3H), 6.00 (d, J=3.2 Hz, 1H), 2.62 (t, J=7.6, 2H), 1.64 (td, J=2H), 1.28-1.34 (m, 6H) 0.87 (t, 3H) ppm. 13C NMR (75 MHz, CDCl3): δ 156.3, 147.0, 144.8, 141.3, 111.3, 106.5, 105.9, 104.1, 31.6, 28.9, 28.1, 28.0, 22.6, 14.1 ppm. HRMS (FD): m/z calcd for C14H18O2: 218.1307. found 218.1315.

Workup

  1. temperaturethe reaction mixture was refluxed under N2 for 5 h
  2. temperatureThe mixture was then cooled
  3. customseparated with hexane
  4. dry with materialthe organic layer was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude product was purified by silica gel column chromatography (elution with hexane)

Sources & evidence

ORD record
ord-d97573fa3f194d7097caf3692ea10187
Source dataset
uspto-grants-2014_06
Patent number
US08759550B2

Reaction notes

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