反応式
[CH3:1][C:2]([C:4]1[CH:5]=[CH:6][C:7]([OH:10])=[CH:8][CH:9]=1)=[O:3].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O[CH2:31][CH2:32][NH:33][C:34](=[O:43])[O:35][CH2:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1.N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O>C1(C)C=CC=CC=1.O1CCCC1>[CH2:36]([O:35][C:34](=[O:43])[NH:33][CH2:32][CH2:31][O:10][C:7]1[CH:8]=[CH:9][C:4]([C:2](=[O:3])[CH3:1])=[CH:5][CH:6]=1)[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1参加物
反応条件
- 温度
- 0 °C
実験手順
In around-bottomed flask equipped with a mechanical stirrer, 4-hydroxyacetophenone (5.00 g, 36.7 mmol) was dissolved in toluene (122 ml), and triphenylphosphine (14.4 g, 55.1 mmol), and benzyl N-(2-hydroxyethyl)carbamate (10.8 g, 55.1 mmol) were added. The reaction mixture was cooled to about 0° C., and 1,1′-(azodicarbonyl)dipiperidine (13.9 g, 55.1 mmol) was added in one portion. The mixture was allowed to warm to room temperature, and after stirring for about ten minutes, an additional 122 ml of toluene and 122 ml of tetrahydrofuran were added to the thick orange solution. The mixture was stirred for an additional twenty-four hours, and the solids were filtered off. The filtrate was concentrated in vacuo and the resulting solid was purified by column chromatography (silica gel; hexanes to 2:1 hexanes/ethyl acetate) to afford 9.68 g (84% yield) of the desired product as a white solid. LRMS ([M−1]−)=312.2.
後処理
- customIn around-bottomed flask equipped with a mechanical stirrer
- temperatureto warm to room temperature
- stirringThe mixture was stirred for an additional twenty-four hours
- filtrationthe solids were filtered off
- concentrationThe filtrate was concentrated in vacuo
- customthe resulting solid was purified by column chromatography (silica gel; hexanes to 2:1 hexanes/ethyl acetate)
出典と根拠
- ORDレコード
- ord-1dcad41ea8404f2bacfac8d166926bef
- 出典データセット
- uspto-grants-2004_03
- 特許番号
- US06706743B2
関連ノート
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