反応 #464486

反応方程式

2-[(1RS,2SR)-1-hydroxy-2-[(3-methoxyphenyl)methyl]cyclohexyl]-4,5-diphenyloxazole

DL-methionine

DL-methionine

→

2-[6-[(3-hydroxyphenyl)methyl]-1-cyclohexen-1-yl]-4,5-diphenyloxazole

収率 43.4%

溶媒

methanesulfonic acid

methanesulfonic acid

反応条件

後処理

1. 1
   workup.STIRRINGThe mixture was stirred at the same temperature for 23 hours
2. 2
   抽出The resulting aqueous mixture was extracted three times with ethyl acetate
3. 3
   洗浄washed with sodium bicarbonate aqueous solution and brine
4. 4
   乾燥dried over magnesium sulfate
5. 5
   その他evaporated in vacuo
6. 6
   その他The residue was chromatographed (n-hexane-diethyl ether (100:20)) over silica gel

実験手順

A suspension of 2-[(1RS,2SR)-1-hydroxy-2-[(3-methoxyphenyl)methyl]cyclohexyl]-4,5-diphenyloxazole (2.23 g) and DL-methionine (7.56 g) in methanesulfonic acid (33.0 ml) was stirred at 60° C. for 17 hours, then another DL-methionine (7.56 g) and methanesulfonic acid (33.0 ml) was added thereto. The mixture was stirred at the same temperature for 23 hours and poured into ice-water. The resulting aqueous mixture was extracted three times with ethyl acetate. The extracts were combined, washed with sodium bicarbonate aqueous solution and brine, dried over magnesium sulfate, and evaporated in vacuo. The residue was chromatographed (n-hexane-diethyl ether (100:20)) over silica gel. The first eluate afforded 2-[6-[(3-hydroxyphenyl)methyl]-1-cyclohexen-1-yl]-4,5-diphenyloxazole (897 mg) as paste.

出典