Methanol → HCID 19360028, 화합물

HRID 376839노트

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HRID 376839 반응식
[OH:1][C:2]1[O:6]N[C:4](=[O:7])[C:3]=1[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[CH2:14][O:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[CH3:22].[CH3:23]O.C[Si]([CH:29]=[N+:30]=[N-])(C)C>C1(C)C=CC=CC=1.O>[CH3:23][O:6][C:2]1[O:1][N:30]([CH3:29])[C:4](=[O:7])[C:3]=1[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[CH2:14][O:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[CH3:22]

참가 물질

6

반응물 3

HCID 887MethanolHCID 167693TrimethylsilyldiazomethaneHCID 193600335-Hydroxy-4-{2-[(2-methylphenoxy)methyl]phenyl}-1,2-oxazol-3(2H)-one

생성물 1

HCID 19360028HCID 19360028, 화합물수율 13%

시약·촉매·용매 2

HCID 962Water용매HCID 1140Toluene용매

반응 조건

온도
25 °C

실험 절차

5-Hydroxy-4-[2-[(2-methylphenoxy)methyl]phenyl]-3(2H)-isoxazolone (31.3 g) was dissolved in 330 mL of 10:1 toluene:methanol and cooled in an ice-water bath. Trimethylsilyl-diazomethane (~2M in hexane) (55 mL) was added dropwise. Gas evolution was observed. The yellow solution was stirred at 25° C. for 2 h. The solution was diluted with 100 mL of water and extracted with ethyl acetate (4×100 mL). The combined organic extracts were dried (Mg SO4), filtered and concentrated under reduced pressure to yield an oil, which was purified by flash chromatography (silica gel; 1:1 hexane:ethyl acetate as eluant). The second eluting component was collected to yield 4.35 g (13%) of the title compound of Step E as a white solid, mp 90-92° C. 1H NMR (CDCl3) δ 7.61(d,1H), 7.35(m,3H), 7.12(m,2H), 6.84(m,2H), 5.12(s,2H), 3.96(s,3H), 3.41(s,3H), 2.24(s, 3H).

후처리

  1. extractionextracted with ethyl acetate (4×100 mL)
  2. dry with materialThe combined organic extracts were dried (Mg SO4)
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customto yield an oil, which
  6. customwas purified by flash chromatography (silica gel; 1:1 hexane:ethyl acetate as eluant)
  7. customThe second eluting component was collected

출처 및 근거

ORD 기록
ord-b06d55b726a444b3a5ea4f648c60cc7c
출처 데이터셋
uspto-grants-2000_02
특허 번호
US06022870

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