Diethyl Ether → 3-(2H-benzo[d][1,2,3]triazol-2-yl)-2-hydroxy-5-methoxybenzyl methacrylate

HRID 1517761

Reaktionsgleichung

Reaktionsgleichung von HRID 1517761
[N:1]1[N:2]([C:10]2[CH:15]=[C:14]([O:16][CH3:17])[CH:13]=[C:12]([CH2:18][OH:19])[C:11]=2[OH:20])[N:3]=[C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=12.C(N(CC)CC)C.[C:28](Cl)(=[O:32])[C:29]([CH3:31])=[CH2:30].C(OCC)C>C1COCC1>[C:28]([O:19][CH2:18][C:12]1[CH:13]=[C:14]([O:16][CH3:17])[CH:15]=[C:10]([N:2]2[N:3]=[C:4]3[CH:9]=[CH:8][CH:7]=[CH:6][C:5]3=[N:1]2)[C:11]=1[OH:20])(=[O:32])[C:29]([CH3:31])=[CH2:30]

Komponenten

6

Edukt 4

HCID 3283Diethyl EtherHCID 8471TriethylamineHCID 13528Methacryloyl chlorideHCID 669069682-(2H-benzo[d][1,2,3]triazol-2-yl)-6-(hydroxymethyl)-4-methoxyphenol

Produkt 1

HCID 593173993-(2H-benzo[d][1,2,3]triazol-2-yl)-2-hydroxy-5-methoxybenzyl methacrylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
-10 °C

Versuchsvorschrift

In a 250 ml round bottom flask equipped with a magnetic stirrer and nitrogen inlet was dissolved 4.03 g (14.9 mmol) 2-(2H-benzo[d][1,2,3]triazol-2-yl)-6-(hydroxymethyl)-4-methoxyphenol from Example 7 in 50 ml anhydrous THF. Triethylamine (7.4 ml, 53 mmol) was added and the mixture was cooled to −10° C. Methacryloyl chloride (1.99 g, 19.0 mmol) was added dropwise and the mixture was stirred for 1 hr at 0° C. followed by 6 hours at ambient temperature. The mixture was poured into 200 ml diethyl ether and washed with 0.5 N HCl and water. The organic layer was dried with magnesium sulfate, filtered, and concentrated via rotary evaporation to give the desired product as a dark yellow oil which was recrystallized in methanol to give 1.73 g of a light yellow solid (34%). 1H NMR (CDCl3) delta: 11.26 (s, 1H, Ar—OH), 7.92 (d, 2H, Ar—H benzotriazole), 7.91 (s, 1H, Ar—H meta to phenol), 7.49 (d, 2H, Ar—H benzotriazole, 5,6-position), 7.05 (s, 1H, Ar—H meta to phenol), 6.21 (s, 1H, C═C—H trans), 5.61 (s, 1H, C═C—H cis), 5.40 (s, 2H, Ar—CH2), 3.90 (s, 3H, Ar—OCH3), 2.01 (s, 3H, C═C—CH3).

Aufarbeitung

  1. customIn a 250 ml round bottom flask equipped with a magnetic stirrer and nitrogen inlet
  2. waitfollowed by 6 hours at ambient temperature
  3. washwashed with 0.5 N HCl and water
  4. dry with materialThe organic layer was dried with magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated via rotary evaporation

Quellen und Nachweise

ORD-Eintrag
ord-286cd3293ed84b12af9282dd93023ff0
Quelldatensatz
uspto-grants-2012_07
Patentnummer
US08232326B2

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