2,6-Di-tert-butyl-4-methylphenol → HCID 53792035, compound

HRID 375965Notes

Reaction equation

HRID 375965 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:7]=[O:8])[S:5][CH:6]=1.C(C1C=C(C)C=C(C(C)(C)C)C=1O)(C)(C)C.C([Sn](CCCC)(CCCC)[CH:30]=[CH:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH3:41])CCC>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.C1(C)C=CC=CC=1>[CH:30]([C:2]1[CH:3]=[C:4]([CH:7]=[O:8])[S:5][CH:6]=1)=[CH:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH3:41]

Participants

6

Reactant 3

HCID 314042,6-Di-tert-butyl-4-methylphenolHCID 877924-Bromothiophene-2-carbaldehydeHCID 71335010Tributyl(dodec-1-en-1-yl)stannane

Product 1

HCID 53792035HCID 53792035, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Procedure

To a solution of 4-bromo-2-thiophenecarboxaldehyde (35.0), tetrakis(triphenylphosphine)palladium(0) (4.23 g), 2,6-di-t-butyl-4-methylphenol (a few milligrams) and dry toluene (150 ml) was added tri-n-butyl-1-dodecenylstannane (92.0 g), dropwise at room temperature, under nitrogen. The solution was heated under reflux for four hrs, with stirring. After cooling to room temperature, the solution was filtered through a bed of celite, and the filter cake was washed with ether. The filtrate was evaporated and the residue purified by flash chromatography (silica; 5% ethyl acetate-hexane). The appropriate fractions were collected and concentrated. The residue was distilled in a kugelrohr oven (170° C./0.3 mm mercury) to give 46.7 g (92%) of product, as an oil (ca.4:1-trans:cis).

Workup

  1. customdropwise at room temperature
  2. temperatureThe solution was heated
  3. temperatureunder reflux for four hrs
  4. filtrationthe solution was filtered through a bed of celite
  5. washthe filter cake was washed with ether
  6. customThe filtrate was evaporated
  7. customthe residue purified by flash chromatography (silica; 5% ethyl acetate-hexane)
  8. customThe appropriate fractions were collected
  9. concentrationconcentrated
  10. distillationThe residue was distilled in a kugelrohr oven (170° C./0.3 mm mercury)

Sources & evidence

ORD record
ord-1a28804374de4e8ea8c32dda8ad43acf
Source dataset
uspto-grants-1996_01
Patent number
US05488063

Reaction notes

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