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

HRID 1594562

반응식

HRID 1594562 반응식
[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

참가 물질

5

반응물 2

HCID 6346DiiodomethaneHCID 6377974-Chlorocinnamic acid

생성물 1

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

시약·촉매·용매 2

HCID 23994Zinc촉매HCID 6344Dichloromethane용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-0c509964b5f4475f92c823f3b0564e0a
출처 데이터셋
uspto-grants-2001_09
특허 번호
US06284761B1

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