Dichloromethane → METHYL 3-PHENYLETHYNYL-BENZOATE

HRID 2421650Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2421650
I[C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].[C:12]1([C:18]#[CH:19])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.N1CCCCC1.C(Cl)Cl>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.O>[C:12]1([C:18]#[C:19][C:2]2[CH:3]=[C:4]([CH:9]=[CH:10][CH:11]=2)[C:5]([O:7][CH3:8])=[O:6])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Komponenten

7

Edukt 4

HCID 6344DichloromethaneHCID 8082PiperidineHCID 10821PhenylacetyleneHCID 69258Methyl 3-iodobenzoate

Produkt 1

HCID 11053642METHYL 3-PHENYLETHYNYL-BENZOATE

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418476HCID 178418476, VerbindungKatalysatorHCID 962WaterLösungsmittel

Versuchsvorschrift

Methyl 3-iodobenzoate, phenylacetylene (1.5 eq.) and Pd(PPh3)2Cl2 (5 mol %) in piperidine (3 eq.) was heated at 70° C. for 30 minutes. The solidified residue was dissolved with CH2Cl2 and water and poured onto HCl 2N. The acidic phase was extracted three times with CH2Cl2. The combined organic layers were washed twice with HCl 2N, once with water and once with brine. The organic layer was then dried over MgSO4 and concentrated. The resulting residue was purified using SiO2 with petroleum spirit/toluene 70:30 to give methyl 3-phenylethynyl-benzoate as a white solid (quantitative yield). NMR 1H (ppm, CDCl3): 8.20 (t, J4=1.7 Hz, 1H), 7.98 (d, J3=7.9 Hz, 1H), 7.69 (d, J3=7.6 Hz, 1H), 7.54-7.50 (m, 2H), 7.42 (t, J3=7.8 Hz, 1H), 7.36-7.31 (m, 3H), 3.92 (s, 3H).

Aufarbeitung

  1. additionpoured onto HCl 2N
  2. extractionThe acidic phase was extracted three times with CH2Cl2
  3. washThe combined organic layers were washed twice with HCl 2N, once with water and once with brine
  4. dry with materialThe organic layer was then dried over MgSO4
  5. concentrationconcentrated
  6. customThe resulting residue was purified

Quellen und Nachweise

ORD-Eintrag
ord-9c63c7a6521247f89e8537bf746ca42c
Quelldatensatz
uspto-grants-2011_06
Patentnummer
US07956216B2

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