Triethylamine → 2-hydroxy-5-methoxy-3-(5-methoxy-2H-benzo[d][1,2,3]triazol-2-yl)benzyl methacrylate

HRID 1517767ノート

反応式

HRID 1517767 の反応式
[OH:1][CH2:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=[C:5]([N:11]2[N:15]=[C:14]3[CH:16]=[CH:17][C:18]([O:20][CH3:21])=[CH:19][C:13]3=[N:12]2)[C:4]=1[OH:22].C(N(CC)CC)C.[C:30](Cl)(=[O:34])[C:31]([CH3:33])=[CH2:32]>C1COCC1>[C:30]([O:1][CH2:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=[C:5]([N:11]2[N:15]=[C:14]3[CH:16]=[CH:17][C:18]([O:20][CH3:21])=[CH:19][C:13]3=[N:12]2)[C:4]=1[OH:22])(=[O:34])[C:31]([CH3:33])=[CH2:32]

参加物

5

反応物 3

HCID 8471TriethylamineHCID 13528Methacryloyl chlorideHCID 669069922-(hydroxymethyl)-4-methoxy-6-(5-methoxy-2H-benzo[d][1,2,3]triazol-2-yl)phenol

生成物 1

HCID 593174042-hydroxy-5-methoxy-3-(5-methoxy-2H-benzo[d][1,2,3]triazol-2-yl)benzyl methacrylate

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-5 °C

実験手順

The esterification was carried out using the product from Example 11. In a 100 ml round bottom 3-neck flask equipped with a magnetic stirrer and nitrogen inlet was dissolved 3.24 g (10.8 mmol) 2-(hydroxymethyl)-4-methoxy-6-(5-methoxy-2H-benzo[d][1,2,3]triazol-2-yl)phenol in 60 ml anhydrous THF. Triethylamine (1.2 ml) was added and the mixture was cooled to −10-0° C. Methacryloyl chloride (1.40 g, 13.4 mmol) was added dropwise and the mixture was stirred for 2 hr at 0° C. followed by 20 hours at ambient temperature. The salts were filtered off and the filtrate was poured into 100 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 ethanol to give a light yellow solid. 1H NMR (CDCl3) delta: 11.20 (s, 1H, phenol OH), 7.80 (m, 1H, Ar—H benzotriazole), 7.77 (s, 1H, Ar—H phenol), 7.17 (m, 1H, Ar—H benzotriazole), 7.14 (s, 1H, Ar—H phenol), 7.10 (m, 1H, Ar—H benzotriazole), to 6.21 (s, 1H, C═C—H trans), 5.61 (s, 1H, C═C—H cis), 5.38 (s, 2H, Ar—CH2), 3.92 (s, 3H, Ar—OCH3, phenol), 3.88 (s, 3H, Ar—OCH3, benzotriazole), 2.01 (s, 3H, C═C—CH3).

後処理

  1. customIn a 100 ml round bottom 3-neck flask equipped with a magnetic stirrer and nitrogen inlet
  2. waitfollowed by 20 hours at ambient temperature
  3. filtrationThe salts were filtered off
  4. additionthe filtrate was poured into 100 ml diethyl ether
  5. washwashed with 0.5 N HCl and water
  6. dry with materialThe organic layer was dried with magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated via rotary evaporation

出典と根拠

ORDレコード
ord-d4dab10fdba2491ba2db092e750e2b2e
出典データセット
uspto-grants-2012_07
特許番号
US08232326B2

反応ノート

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