Methyl iodide → tert-Butyl 3-(3-(1-methyl-1H-1,2,3-triazol-4-yl)phenethoxy)propanoate

HRID 909895노트

반응식

HRID 909895 반응식
CI.[C:3]([C:5]1[CH:6]=[C:7]([CH:20]=[CH:21][CH:22]=1)[CH2:8][CH2:9][O:10][CH2:11][CH2:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])#[CH:4].[N-:23]=[N+:24]=[N-:25].[Na+].[C:27](O)(C)(C)C>C(OCC)(=O)C.N.[Cu]I.O>[CH3:27][N:23]1[CH:4]=[C:3]([C:5]2[CH:6]=[C:7]([CH:20]=[CH:21][CH:22]=2)[CH2:8][CH2:9][O:10][CH2:11][CH2:12][C:13]([O:15][C:16]([CH3:18])([CH3:19])[CH3:17])=[O:14])[N:25]=[N:24]1

참가 물질

9

반응물 4

HCID 6328Methyl iodideHCID 6386tert-ButanolHCID 33557Sodium AzideHCID 86641259Tert-butyl 3-(3-ethynylphenethoxy)propanoate

생성물 1

HCID 67075980tert-Butyl 3-(3-(1-methyl-1H-1,2,3-triazol-4-yl)phenethoxy)propanoate

시약·촉매·용매 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 222Ammonia용매HCID 962Water용매HCID 8857Ethyl Acetate용매

반응 조건

온도
70 °C

실험 절차

Methyl iodide (0.20 mL) was added in one portion to a mixture of tert-butyl 3-(3-ethynylphenethoxy)propanoate [Example 4, Step ii)] (682 mg), sodium azide (194 mg), tert-butanol (0.750 mL), water (3 mL) and copper (I) iodide (47 mg) and sealed into a microwave tube. The reaction was heated to 70° C., over a period of 2 h in the microwave reactor. The reaction mixture was diluted with ethyl acetate and 35% ammonia was added. The mixture was stirred for 30 min and separated. The organic layer was dried over magnesium sulfate, filtered and evaporated to afford crude product. The crude product was purified by flash silica chromatography, elution gradient 20-100% ethyl acetate in isohexane then elution gradient 0-10% methanol in ethyl acetate to afford the subtitled compound (500 mg). 1H NMR (300 MHz, CDCl3) δ 7.77 (s, 1H), 7.70 (s, 1H), 7.65 (d, J=7.9 Hz, 1H), 7.33 (t, J=7.7 Hz, 1H), 7.19 (d, J=7.7 Hz, 1H), 4.15 (s, 3H), 3.73-3.66 (m, 4H), 2.92 (t, J=7.0 Hz, 2H), 2.49 (t, J=6.4 Hz, 2H), 1.43 (s, 9H).

후처리

  1. customsealed into a microwave tube
  2. additionwas added
  3. customseparated
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customto afford crude product
  8. customThe crude product was purified by flash silica chromatography, elution gradient 20-100% ethyl acetate in isohexane
  9. washelution gradient 0-10% methanol in ethyl acetate

출처 및 근거

ORD 기록
ord-5ea8aefa47dc436bafa06c363c62a8fe
출처 데이터셋
uspto-grants-2011_09
특허 번호
US08017602B2

반응 노트

불러오는 중…