Triethylamine → HCID 86679257, compound

HRID 1519676Notes

Reaction equation

HRID 1519676 reaction equation
C(N([CH2:6][CH3:7])CC)C.I[C:9]1[CH:19]=[CH:18][C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:11][CH:10]=1>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.[Cu]I.C1COCC1>[CH:13]([C:12]1[CH:18]=[CH:19][C:9]([C:6]#[C:7][C:9]2[CH:19]=[CH:18][C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:11][CH:10]=2)=[CH:10][CH:11]=1)=[O:14]

Participants

6

Reactant 2

HCID 8471TriethylamineHCID 142891Ethyl 4-iodobenzoate

Product 1

HCID 86679257HCID 86679257, compoundYield 69%

Reagents, catalysts & solvents 3

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

Procedure

4-Ethynylbenzaldehyde (10 g) obtained by the same method as the synthesis method described in the literature (Tetrahedron Letters, 2007, Vol. 48(33), pp. 5817-5820), PdCl2(PPh3)2 (3.4 g), CuI (1.5 g), and triethylamine (32 mL) were added to a THF (0.25 L) solution of ethyl 4-iodobenzoate (20 g). The mixture was stirred for 3 hours at room temperature, and the reaction mixture was concentrated. The resulting residue was purified by OH type silica gel chromatography (gradient elution with hexane/chloroform=80/20→0/100) to obtain ethyl 4-[(4-formylphenyl)ethynyl]benzoate (yellow solid) (16 g, 69%).

Workup

  1. concentrationthe reaction mixture was concentrated
  2. customThe resulting residue was purified by OH type silica gel chromatography (gradient elution with hexane/chloroform=80/20→0/100)

Sources & evidence

ORD record
ord-e3329296397c491ba52edc36620ca551
Source dataset
uspto-grants-2015_07
Patent number
US09073821B2

Reaction notes

Loading…