Dichloromethane → 2-Chloro-3-(4-methoxyphenyl)propanal

HRID 500108노트

반응식

HRID 500108 반응식
[Cl:1]N1C(=O)CCC1=O.[CH3:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([CH2:17][CH2:18][CH:19]=[O:20])=[CH:13][CH:12]=1.ClCCl>N1CCC[C@@H]1C(O)=O>[Cl:1][CH:18]([CH2:17][C:14]1[CH:15]=[CH:16][C:11]([O:10][CH3:9])=[CH:12][CH:13]=1)[CH:19]=[O:20]

참가 물질

5

반응물 3

HCID 6344DichloromethaneHCID 31398ChlorosuccinimideHCID 111266073-(4-Methoxyphenyl)propanal

생성물 1

HCID 121027562-Chloro-3-(4-methoxyphenyl)propanal수율 71%

시약·촉매·용매 1

HCID 8988D-Proline촉매

실험 절차

N-Chlorosuccinimide (980 mg, 0.0073 mol) was added to a mixture of 3-(4-methoxyphenyl)propanal (1.0 g, 6.1 mmol) and D-proline (40 mg, 0.3 mmol) in dichloromethane (10 mL, 200 mmol) at 0° C. The reaction mixture was warmed to RT after 1 h, quenched with water, and extracted with dichloromethane. The organic extracts were washed with brine, dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by flash chromatography eluting with ethyl acetate in hexanes to give the desired product (860 mg). 1H NMR (400 MHz, CDCl3): 9.52 (s, 1H), 7.18 (dd, 2H), 6.84 (dd, 2H), 4.36 (m, 1H), 3.80 (s, 3H), 3.32 (m, 1H), 3.02 (m, 1H).

후처리

  1. customquenched with water
  2. extractionextracted with dichloromethane
  3. washThe organic extracts were washed with brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by flash chromatography
  8. washeluting with ethyl acetate in hexanes

출처 및 근거

ORD 기록
ord-9e6a8d100dbb427daa02525f0451b8c6
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07767675B2

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