Diiodomethane → rac-(1R,2R)-2-(4-chlorophenyl)cyclopropane-1-carboxylic acid

HRID 1594562ノート

反応式

HRID 1594562 の反応式
[CH2:1](I)I.[Cl:4][C:5]1[CH:15]=[CH:14][C:8](/[CH:9]=[CH:10]/[C:11]([OH:13])=[O:12])=[CH:7][CH:6]=1>C(Cl)Cl.[Zn]>[Cl:4][C:5]1[CH:6]=[CH:7][C:8]([C@@H:9]2[CH2:1][C@H:10]2[C:11]([OH:13])=[O:12])=[CH:14][CH:15]=1

参加物

5

反応物 2

HCID 6346DiiodomethaneHCID 6377974-Chlorocinnamic acid

生成物 1

HCID 6993920rac-(1R,2R)-2-(4-chlorophenyl)cyclopropane-1-carboxylic acid

試薬・触媒・溶媒 2

HCID 23994Zinc触媒HCID 6344Dichloromethane溶媒

実験手順

A mixture of zinc dust (6.54 g, 0.1 mole) and cuprous chloride (1 g, 0.01 mole) in methylene chloride (30 mL) is stirred and heated to reflux under a nitrogen atmosphere for 30 min. After the mixture is cooled to room temperature, methylene iodide (13.4 g, 0.05 mole) is added to the mixture which is then refluxed for an additional hour. After cooling to 0° C., trans-4-chlorocinnamic acid (9.1 g) is added. The reaction is allowed to warm to room temperature over 2 hours and then refluxed for 3 days. The reaction is quenched at 0° C. by the addition of 30 ml of diethyl ether and 30 ml of ice cold 10% H2SO4 solution. The mixture is filtered washed with ether. The organic layer is dried over MgSO4 and concentrated to provide the desired product as a white solid. 1H NMR (CDCl3) 7.25 (d, J=7 Hz, 2H), 7.05 (d, J=7 Hz, 2H), 2.58 (m, 1H), 1.85 (m, 1H), 1.65 (m, 1H), 1.37 (m, 1H).

後処理

  1. temperatureheated
  2. temperatureto reflux under a nitrogen atmosphere for 30 min
  3. temperatureis then refluxed for an additional hour
  4. temperatureAfter cooling to 0° C.
  5. temperatureto warm to room temperature over 2 hours
  6. temperaturerefluxed for 3 days
  7. customThe reaction is quenched at 0° C. by the addition of 30 ml of diethyl ether and 30 ml of ice cold 10% H2SO4 solution
  8. filtrationThe mixture is filtered
  9. washwashed with ether
  10. dry with materialThe organic layer is dried over MgSO4
  11. concentrationconcentrated

出典と根拠

ORDレコード
ord-0c509964b5f4475f92c823f3b0564e0a
出典データセット
uspto-grants-2001_09
特許番号
US06284761B1

反応ノート

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