Ethyl Acetate → 5-Chloro-2-(chloromethyl)pyridine

HRID 271472

반응식

HRID 271472 반응식
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8]O)=[N:6][CH:7]=1.S(Cl)([Cl:12])=O.CCOC(C)=O.C([O-])([O-])=O.[Na+].[Na+]>ClCCl.CN(C=O)C.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][Cl:12])=[N:6][CH:7]=1

참가 물질

8

반응물 4

HCID 8857Ethyl AcetateHCID 10340Sodium CarbonateHCID 24386Thionyl ChlorideHCID 20537893(5-Chloropyridin-2-yl)methanol

생성물 1

HCID 145171515-Chloro-2-(chloromethyl)pyridine수율 89.4%

시약·촉매·용매 3

HCID 6228Dimethylformamide촉매HCID 962Water용매HCID 6344Dichloromethane용매

실험 절차

To a stirring solution of (5-chloropyridin-2-yl)methanol (840 mg, 5.8 mmol) in dichloromethane (10 mL) at 0° C. under argon was added thionyl chloride (0.64 mL, 8.77 mmol), followed by 4 drops of DMF (white precipitate formed). The reaction mixture was allowed to stir at room temperature for 1 h. The reaction mixture was concentrated to a white solid. The solid thus obtained was cooled in an ice bath before EtOAc (20 mL) and water (20 mL) and then 10% aqueous Na2CO3 solution (20 mL) were added. The organic layer was separated, washed with saturated aqueous NaCl, dried (MgSO4), filtered and concentrated to obtain 840 mg of the title compound as a light brown gum. HPLC/MS: retention time=2.392 min, [M+H]+=162.

후처리

  1. concentrationThe reaction mixture was concentrated to a white solid
  2. customThe solid thus obtained
  3. customThe organic layer was separated
  4. washwashed with saturated aqueous NaCl
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated

출처 및 근거

ORD 기록
ord-9f8450a03e8f493db052c87b82442419
출처 데이터셋
uspto-grants-2008_11
특허 번호
US07452892B2

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