Pyridine → 9-Anthrylmethyl methacrylate

HRID 1748931

반응식

HRID 1748931 반응식
[CH:1]1[C:14]2[C:5](=[CH:6][C:7]3[C:12]([C:13]=2[CH2:15][OH:16])=[CH:11][CH:10]=[CH:9][CH:8]=3)[CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.N1C=CC=CC=1.[C:30](Cl)(=[O:34])[C:31]([CH3:33])=[CH2:32]>C1COCC1>[C:30]([O:16][CH2:15][C:13]1[C:12]2[C:7]([CH:6]=[C:5]3[C:14]=1[CH:1]=[CH:2][CH:3]=[CH:4]3)=[CH:8][CH:9]=[CH:10][CH:11]=2)(=[O:34])[C:31]([CH3:33])=[CH2:32]

참가 물질

6

반응물 4

HCID 1049PyridineHCID 8471TriethylamineHCID 13528Methacryloyl chlorideHCID 738489-Anthracenemethanol

생성물 1

HCID 36187549-Anthrylmethyl methacrylate

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
0 °C

실험 절차

9-Anthracenemethanol (30 g) was dissolved in freshly distilled THF (150 mL). To the solution triethylamine (30 mL) and pyridine (20 mL) were added and the mixture was cooled down to 0° C. Then methacryloyl chloride (21 mL) was added dropwise. After the addition, ice-water bath was removed and the mixture was stirred for 1 hour. After water (75 mL) was added to the reaction flask, the solution was transferred into separatory funnel and extracted with diethyl ether (500 mL). The extract was washed with aqueous HCl (1 M, 150 mL), aqueous NaHCO3 (5%, 150 mL), and brine (150 mL), respectively. The solvent was evaporated in vacuum and recrystallized with methanol. (Product: 21 g) 1H NMR (500 MHz, CDCl3): δ 8.55 (s, 1H), 8.41 (d, J=8.9 Hz, 2H), 8.07 (d, J=8.4 Hz, 2H), 7.61 (t, J=7.7 Hz, 2H), 7.53 (t, J=7.9 Hz, 2H), 6.25 (s, 2H), 6.08 (s, 1H), 5.54 (s, 1H), 1.95 (s, 3H) ppm.

후처리

  1. customwas removed
  2. additionAfter water (75 mL) was added to the reaction flask
  3. customthe solution was transferred into separatory funnel
  4. extractionextracted with diethyl ether (500 mL)
  5. washThe extract was washed with aqueous HCl (1 M, 150 mL), aqueous NaHCO3 (5%, 150 mL), and brine (150 mL)
  6. customThe solvent was evaporated in vacuum
  7. customrecrystallized with methanol

출처 및 근거

ORD 기록
ord-1980f3b4a9864438b3fc817b8bcccb0a
출처 데이터셋
uspto-grants-2015_10
특허 번호
US09153353B2

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