Trimethyl orthoacetate → 5-Methoxy-2-methylbenzoxazole
反応式
[NH2:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][C:3]=1[OH:10].[C:11](OC)(OC)(OC)[CH3:12]>>[CH3:9][O:8][C:6]1[CH:5]=[CH:4][C:3]2[O:10][C:11]([CH3:12])=[N:1][C:2]=2[CH:7]=1参加物
3
実験手順
A solution of 2-amino-4-methoxyphenol 17 (8 g, 57.4 mmol) in trimethyl orthoacetate 18 (50 mL) was heated to reflux and allowed to stir for 24 h. The reaction was allowed to cool and the excess 18 was evaporated (in vacuo). The residue was dissolved in ethyl acetate and washed with water. The organic layer was dried over MgSO4 and treated with activated carbon Norit A. The resulting solution was filtered through Celite 521 and evaporated to yield an oil. The oil was chromatographed on silica gel (20% ethyl acetate/hexanes) to yield compound 19 as a light yellow solid. Synthesis of 2-methyl-5-oxiran-2-ylmethoxybenzoxazole (67):
後処理
- temperatureto reflux
- temperatureto cool
- customthe excess 18 was evaporated (in vacuo)
- dissolutionThe residue was dissolved in ethyl acetate
- washwashed with water
- dry with materialThe organic layer was dried over MgSO4
- additiontreated with activated carbon Norit A
- filtrationThe resulting solution was filtered through Celite 521
- customevaporated
- customto yield an oil
- customThe oil was chromatographed on silica gel (20% ethyl acetate/hexanes)
出典と根拠
- ORDレコード
- ord-c0bca52f05014ddbbde713850ce9dfda
- 出典データセット
- uspto-grants-2005_02
- 特許番号
- US06849632B2
反応ノート
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