Triethylamine → HCID 117899529, compound

HRID 926996Notes

Reaction equation

HRID 926996 reaction equation
I[C:2]1[CH:9]=[CH:8][C:5]([CH2:6][OH:7])=[CH:4][CH:3]=1.[CH:10]([CH:12]1[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1)=[CH2:11].C(N(CC)CC)C>CN(C=O)C.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl>[CH:12]1(/[CH:10]=[CH:11]/[C:2]2[CH:9]=[CH:8][C:5]([CH2:6][OH:7])=[CH:4][CH:3]=2)[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 12757VinylcyclohexaneHCID 290124-Iodobenzyl alcohol

Product 1

HCID 117899529HCID 117899529, compoundYield 31.1%

Reagents, catalysts & solvents 2

HCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

4-Iodobenzyl alcohol (2.34 g) was dissolved in DMF (40 mL), added with vinylcyclohexane (1.32 g), triethylamine (1.81 mL), and bis(triphenylphosphine)palladium (II) chloride (700 mg), and stirred for 23 hours at 80° C. After cooling to room temperature, the solvent was evaporated under reduced pressure, and the residues were purified by silica gel column chromatography (8 to 30% ethyl acetate/hexane) to obtain the title compound (672 mg) as a yellow solid.

Workup

  1. temperatureAfter cooling to room temperature
  2. customthe solvent was evaporated under reduced pressure
  3. customthe residues were purified by silica gel column chromatography (8 to 30% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-b8e76cea2d2a4d4b8b604ce73e94e741
Source dataset
uspto-grants-2016_03
Patent number
US09290440B2

Reaction notes

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