Triethylamine → HCID 123643465, compound

HRID 625906Notes

Reaction equation

HRID 625906 reaction equation
C(N(CC)CC)C.[C:8]([O:11][CH2:12][CH:13]=[C:14]([CH3:18])[C:15](Cl)=[O:16])(=[O:10])[CH3:9].[CH3:19][C:20]1[CH2:25][CH2:24][CH2:23][C:22]([CH3:27])([CH3:26])[C:21]=1[CH2:28][CH:29]=[C:30]([CH3:33])[C:31]#[CH:32]>[Cu]I.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.C1COCC1>[C:8]([O:11][CH2:12][CH:13]=[C:14]([CH3:18])[C:15](=[O:16])[C:32]#[C:31][C:30]([CH3:33])=[CH:29][CH2:28][C:21]1[C:22]([CH3:27])([CH3:26])[CH2:23][CH2:24][CH2:25][C:20]=1[CH3:19])(=[O:10])[CH3:9]

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 77985402HCID 77985402, compoundHCID 78088935HCID 78088935, compound

Product 1

HCID 123643465HCID 123643465, compound

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Under inert gas atmosphere 59.9 mg (0.308 mmol) of copper(I) iodide and 110.3 mg (0.154 mmol) of bis(triphenylphosphine)palladium(II) dichloride [(PPh3)2PdCl2] were added to a 100 ml four-necked flask. At 23° C., 42.0 ml of anhydrous THF were added and the yellow suspension was stirred for 5 min. When 2.15 ml (15.4 mmol) of triethylamine were introduced drop wise via syringe an orange solution was obtained. Within 1 minute 3.10 g (15.4 mmol) of 4-chloro-3-methyl-4-oxobut-2-enyl acetate (compound of formula (IVa)) were added and the solution turned dark orange. Upon drop wise addition of 2.92 g (14.0 mmol) of 1,3,3-trimethyl-2-(3-methylpent-2-en-4-ynyl)cyclohex-1-ene (compound of formula (III))

Workup

  1. customwas obtained

Sources & evidence

ORD record
ord-963571c9de644547bd12b8c2ef28996d
Source dataset
uspto-grants-2016_04
Patent number
US09309194B2

Reaction notes

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