Pyridine → [2-Methoxy-1-(3-methylbutyl)-1,4-dihydronaphthalen-1-yl]methyl acetate

HRID 2224979노트

반응식

HRID 2224979 반응식
[CH3:1][O:2][C:3]1[C:4]([CH2:18][OH:19])([CH2:13][CH2:14][CH:15]([CH3:17])[CH3:16])[C:5]2[C:10]([CH2:11][CH:12]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2.[C:20](OC(=O)C)(=[O:22])[CH3:21].N1C=CC=CC=1>O>[C:20]([O:19][CH2:18][C:4]1([CH2:13][CH2:14][CH:15]([CH3:16])[CH3:17])[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH2:11][CH:12]=[C:3]1[O:2][CH3:1])(=[O:22])[CH3:21]

참가 물질

5

반응물 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 68871071[2-Methoxy-1-(3-methylbutyl)-1,4-dihydronaphthalen-1-yl]methanol

생성물 1

HCID 68872462[2-Methoxy-1-(3-methylbutyl)-1,4-dihydronaphthalen-1-yl]methyl acetate수율 81%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

A mixture of Example 179A (0.18 g, 0.7 mmol), acetic anhydride (0.2 mL), and pyridin (1 mL) was stirred at room temperature for 18 h. The solution was diluted with water (3 mL) and extracted with ethyl acetate (2×1 mL). The combined organic extracts were dried (Na2SO4) and concentrated in vacuo. Column chromatography on silica (hexane to 5% ethyl acetate/hexane) afforded product as a colorless oil (0.17 g, 81%). 1H NMR (300 MHz, CDCl3) δ ppm 0.66 (m, 1 H), 0.76 (dd, J=9.56, 6.62 Hz, 6 H), 0.89 (m, 1 H), 1.38 (m, 1 H), 1.61 (m, 1 H), 1.81 (s, 3 H), 1.95 (m, 1 H), 3.50 (s, 2 H), 3.58 (s, 3 H), 4.24 (d, J=10.66 Hz, 1 H), 4.42 (d, J=10.66 Hz, 1 H), 5.01 (t, J=3.49 Hz, 1 H), 7.20 (m, 4 H).

후처리

  1. extractionextracted with ethyl acetate (2×1 mL)
  2. dry with materialThe combined organic extracts were dried (Na2SO4)
  3. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-20c842f3a0944532b56f96cf00d78459
출처 데이터셋
uspto-grants-2008_05
특허 번호
US07378414B2

반응 노트

불러오는 중…