Diisopropylamine → HCID 86754018, compound

HRID 1420294Notes

Reaction equation

HRID 1420294 reaction equation
I[C:2]1[C:8](I)=[C:7]([OH:10])[C:6]([CH3:11])=[C:5]([CH3:12])[C:3]=1[OH:4].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C(NC(C)C)(C)C.[CH3:39][Si:40]([C:43]#[CH:44])([CH3:42])[CH3:41]>[Pd].C1(C)C=CC=CC=1>[CH3:39][Si:40]([CH3:42])([CH3:41])[C:43]#[C:44][C:2]1[C:8]([Si:40]([CH3:42])([CH3:41])[CH3:39])=[C:7]([OH:10])[C:6]([CH3:11])=[C:5]([CH3:12])[C:3]=1[OH:4]

Participants

7

Reactant 4

HCID 7912DiisopropylamineHCID 11776TriphenylphosphineHCID 66111TrimethylsilylacetyleneHCID 11090406HCID 11090406, compound

Product 1

HCID 86754018HCID 86754018, compoundYield 50.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 1140TolueneSolvent

Procedure

To a degassed solution of 2,3-diiodo 5,6-dimethylhydroquinone (1)(3.6 g, 9.23 mmol), Pd"(PhCN)2Cl2 (176.9 mg, 0.46 mmol), PPh3 (278.2 mg, 1.06 mmol), and Cul (297 mg, 1.56 mmol) in 110 mL to toluene under argon were added 2.5 mL (18.5 mmol) of diisopropylamine and 4.0 mL (28.6 mmol) of (trimethylsilyl)acetylene. After stirring at room temperature for a day the reaction mixture was opened to air, filtered and concentrated under vacuo. Flash column chromatography with 7% ethyl acetate in petroleum ether produced yellow compound (2) with 50.2% yield (1.53 g). Melting point 76°-77° C.

Workup

  1. filtrationfiltered
  2. concentrationconcentrated under vacuo

Sources & evidence

ORD record
ord-495ce80934324dcb9b287bbb062962cf
Source dataset
uspto-grants-1999_03
Patent number
US05889185

Reaction notes

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