Methanol → HCID 19360028、化合物

HRID 1601131ノート

反応式

HRID 1601131 の反応式
[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]

参加物

6

反応物 3

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

生成物 1

HCID 19360028HCID 19360028、化合物収率 13%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 1140Toluene溶媒

反応条件

温度
25 °C

実験手順

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 (MgSO4), 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).

後処理

  1. extractionextracted with ethyl acetate (4×100 mL)
  2. dry with materialThe combined organic extracts were dried (MgSO4)
  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

出典と根拠

ORDレコード
ord-f9e62835c3c44e10be96443de812cc7c
出典データセット
uspto-grants-1999_11
特許番号
US05977149

反応ノート

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