Ethanol → 2-Methyl-2-(4-{2-[5-methyl-2-(4-naphthalen-1-ylphenyl)oxazol-4-yl]ethoxy}-phenoxy) propionic acid ethyl ester

HRID 2417042

Reaktionsgleichung

Reaktionsgleichung von HRID 2417042
[CH2:1]([O:3][C:4](=[O:31])[C:5]([O:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][CH2:17][C:18]2[N:19]=[C:20]([C:24]3[CH:29]=[CH:28][C:27](Br)=[CH:26][CH:25]=3)[O:21][C:22]=2[CH3:23])=[CH:11][CH:10]=1)([CH3:7])[CH3:6])[CH3:2].[C:32]1(B(O)O)[C:41]2[C:36](=[CH:37][CH:38]=[CH:39][CH:40]=2)[CH:35]=[CH:34][CH:33]=1.C(O)C.C([O-])([O-])=O.[Na+].[Na+]>C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:1]([O:3][C:4](=[O:31])[C:5]([CH3:7])([O:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][CH2:17][C:18]2[N:19]=[C:20]([C:24]3[CH:29]=[CH:28][C:27]([C:40]4[C:41]5[C:36](=[CH:35][CH:34]=[CH:33][CH:32]=5)[CH:37]=[CH:38][CH:39]=4)=[CH:26][CH:25]=3)[O:21][C:22]=2[CH3:23])=[CH:11][CH:10]=1)[CH3:6])[CH3:2]

Komponenten

7

Edukt 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 2545321-Naphthaleneboronic acidHCID 110273422-(4-{2-[2-(4-Bromophenyl)-5-methyloxazol-4-yl]ethoxy}phenoxy)-2-methylpropionic acid ethyl ester

Produkt 1

HCID 129668362-Methyl-2-(4-{2-[5-methyl-2-(4-naphthalen-1-ylphenyl)oxazol-4-yl]ethoxy}-phenoxy) propionic acid ethyl ester

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 1140TolueneLösungsmittel

Versuchsvorschrift

A solution of 2-(4-{2-[2-(4-bromophenyl)-5-methyloxazol-4-yl]ethoxy}phenoxy)-2-methyl-propionic acid ethyl ester (0.907 mmol) (see Ex. 2, part B) and 1-naphthaleneboronic acid (0.998 mmol) in toluene:ethanol (18.2 mL of a 1:1 solution) was treated with Na2CO3(aq) (0.906 mL of a 2M solution). A nitrogen atmosphere was applied, Pd(PPh3)4 (52.5 mg) was added, and the orange mixture was heated at reflux for 2 h. After cooling to room temperature, the mixture was partitioned between ethyl acetate (20 mL) and H2O (30 mL). The layers were separated, and the aqueous phase was back-extracted with ethyl acetate (2×10 mL). Combined organic phases were washed with brine (20 mL), dried over Na2SO4, and concentrated. The product was purified by silica gel chromatography (20 g SiO2, 3:7 ethyl acetate:hexanes) to give the desired product in 87% as an orange oil; Rf=0.46 in 1:4 ethyl acetate:hexanes; 1H NMR (400 MHz, CDCl3) δ 8.09 (d, J=8 Hz, 2H), 7.92-7.82 (m, 3H), 7.59-7.40 (m, 6H), 6.81-6.72 (m, 4H), 4.22-4.17 (m, 4H), 2.98 (t, 2H), 2.38 (s, 3H), 1.46 (s, 6H), 1.22 (t, 3H); MS (EI) 536.3 (M+H)+.

Aufarbeitung

  1. temperaturethe orange mixture was heated
  2. temperatureat reflux for 2 h
  3. customthe mixture was partitioned between ethyl acetate (20 mL) and H2O (30 mL)
  4. customThe layers were separated
  5. extractionthe aqueous phase was back-extracted with ethyl acetate (2×10 mL)
  6. washCombined organic phases were washed with brine (20 mL)
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated
  9. customThe product was purified by silica gel chromatography (20 g SiO2, 3:7 ethyl acetate:hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-d1192c7840db488aa1ab0b7d164a3842
Quelldatensatz
uspto-grants-2004_11
Patentnummer
US06825222B2

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