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

HRID 1257768ノート

反応式

HRID 1257768 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

HCID 121027562-Chloro-3-(4-methoxyphenyl)propanal収率 71%

試薬・触媒・溶媒 1

HCID 8988D-Proline触媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-6fe530957cde4a378dcab99723ab0b77
出典データセット
uspto-grants-2013_06
特許番号
US08461330B2

反応ノート

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