丙酮 → 4-[(Methylsulfonyl)methyl]cyclohexanecarboxylic acid

HRID 14316

反应方程式

HRID 14316 反应方程式
CS[CH2:3][CH:4]1[CH2:9][CH2:8][CH:7]([C:10]([OH:12])=[O:11])[CH2:6][CH2:5]1.[C:13](=O)(O)[O-].[Na+].CC(C)=O.O[O:23][S:24]([O-:26])=O.[K+]>[OH-].[Na+].C(N(CC(O)=O)CC(O)=O)CN(CC(O)=O)CC(O)=O>[CH3:13][S:24]([CH2:3][CH:4]1[CH2:9][CH2:8][CH:7]([C:10]([OH:12])=[O:11])[CH2:6][CH2:5]1)(=[O:26])=[O:23]

参与物

7

反应物 4

HCID 180丙酮HCID 516892碳酸氢钠HCID 210859504-[(Methylthio)methyl]cyclohexanecarboxylic acidHCID 23707502Potassium hydroxy sulfite

产物 1

HCID 210859494-[(Methylsulfonyl)methyl]cyclohexanecarboxylic acid收率 90.8%

试剂、催化剂与溶剂 2

HCID 6049乙二胺四乙酸二钠溶剂HCID 14798二甲基对苯二胺二盐酸溶剂

实验过程

To a stirred solution of methyl sulfide from step 5 (100 mg, 0.5 mmol) in sodium hydroxide solution (1.5 mL, 0.5 M solution in water) was added sodium bicarbonate (360 mg, 4.3 mmol) and acetone (1 mL) followed by the addition of a solution of oxone (430 mg, 0.7 mmol) in 0.0004 M EDTA (2 mL). The reaction mixture was stirred at room temperature for 2 h and then quenched with sodium bisulfite. The reaction mixture was acidified with 1 N hydrochloric acid and extracted with ethyl acetate (3×100 mL). The combined organic layers were washed with water, dried (sodium sulfate), filtered, and concentrated under reduced pressure to provide 4-[(methylsulfonyl)methyl]cyclohexanecarboxylic acid (100 mg): 1H NMR (300 MHz, CD3OD) δ 3.11-3.08 (m, 2H), 2.96 (s, 3H), 2.53-2.51 (m, 1H), 2.18-2.16 (m, 1H), 1.99-1.93 (m, 2H), 1.79-1.25 (m, 6H).

后处理

  1. customquenched with sodium bisulfite
  2. extractionextracted with ethyl acetate (3×100 mL)
  3. washThe combined organic layers were washed with water
  4. dry with materialdried (sodium sulfate)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

来源与证据

ORD记录
ord-618f895760604f8f97d25ee748018ef9
来源数据集
uspto-grants-2010_06
专利号
US07727997B2

关联笔记

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