反応 #160380

反応方程式

acetic anhydride

(1R,2S,4R)-2-Hydroxy-4-methyl-cyclohexanecarboxylic acid

pyridine

→

(1R,2S,4R)-2-Acetoxy-4-methyl-cyclohexanecarboxylic acid

収率 53.4%

溶媒

dichloromethane

反応条件

後処理

1. 1
   その他Then, the solvents were removed
2. 2
   workup.ADDITION10 ml of 3N HCl solution was added
3. 3
   workup.STIRRINGThis mixture was stirred for 30 minutes
4. 4
   workup.ADDITIONa saturated solution of NaHCO3 was slowly added until PH=9-10
5. 5
   抽出This solution was then extracted with ethyl acetate (2×5 ml)
6. 6
   抽出extracted with ethyl acetate (3×5 ml)
7. 7
   乾燥dried (Na2SO4)
8. 8
   濃縮concentrated

実験手順

To a solution of (1R,2S,4R)-2-Hydroxy-4-methyl-cyclohexanecarboxylic acid (162 mg, 1.02 mmol) in dichloromethane (5 ml) was added pyridine (495 ul, 6.12 mmol) followed by acetic anhydride (385 ul, 4.08 mmol). The reaction mixture was stirred for 20 h at room temperature. Then, the solvents were removed and 10 ml of 3N HCl solution was added. This mixture was stirred for 30 minutes and then a saturated solution of NaHCO3 was slowly added until PH=9-10. This solution was then extracted with ethyl acetate (2×5 ml). The aqueous phase was then acidified with a 10% HCl solution and extracted with ethyl acetate (3×5 ml). The following ethyl acetate layers were combined, dried (Na2SO4) and concentrated to obtain 109 mg (53%) of (1R,2S,4R)-2-Acetoxy-4-methyl-cyclohexanecarboxylic acid.

出典