Tetrahydrofuran → HCID 86679257, compound

HRID 1519684Notes

Reaction equation

HRID 1519684 reaction equation
C1COCC1.I[C:7]1[CH:17]=[CH:16][C:10]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:9][CH:8]=1.[C:18]([C:20]1[CH:27]=[CH:26][C:23]([CH:24]=[O:25])=[CH:22][CH:21]=1)#[CH:19]>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.O>[CH:24]([C:23]1[CH:26]=[CH:27][C:20]([C:18]#[C:19][C:7]2[CH:17]=[CH:16][C:10]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:9][CH:8]=2)=[CH:21][CH:22]=1)=[O:25]

Participants

7

Reactant 3

HCID 8028TetrahydrofuranHCID 142891Ethyl 4-iodobenzoateHCID 27716454-Ethynylbenzaldehyde

Product 1

HCID 86679257HCID 86679257, compound

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 962WaterSolvent

Procedure

TEA (46 mL) was added to a THF (0.40 L) suspension of ethyl 4-iodobenzoate (30 g), 4-ethynylbenzaldehyde (14 g) obtained by the synthesis method described in the literature (Tetrahedron Letters, 2007, Vol. 48(33), pp. 5817-5820), PdCl2(PPh3)2 (3.9 g), and CuI (2.1 g), and the mixture was stirred for 4 hours at 45° C. After the reaction mixture was allowed to cool, water was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with brine, and dried over anhydrous sodium sulfate. The desiccant was filtered out, and the solvent was distilled off under reduced pressure. Hexane/ethyl acetate (1:1 (v/v)) was added to the resulting residue, the mixture was stirred, and then the precipitate was filtered off and dried. The filtrate was concentrated, and then the same procedure was performed. As a result, ethyl 4-[(4-formylphenyl)ethynyl]benzoate (yellow solid) was obtained (27 g, 88%).

Workup

  1. customobtained by the synthesis method
  2. temperatureto cool
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationThe desiccant was filtered out
  7. distillationthe solvent was distilled off under reduced pressure
  8. additionHexane/ethyl acetate (1:1 (v/v)) was added to the resulting residue
  9. filtrationthe precipitate was filtered off
  10. customdried
  11. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-8d4c67c6af0548a7bc9d07dbd19cbb0f
Source dataset
uspto-grants-2015_07
Patent number
US09073821B2

Reaction notes

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