Sodium borohydride → 2-Cyano 3-(2,6-dichlorophenyl)propanoic acid

HRID 1026622노트

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HRID 1026622 반응식
[BH4-].[Na+].[C:3]([C:5](=[CH:9][C:10]1[C:15]([Cl:16])=[CH:14][CH:13]=[CH:12][C:11]=1[Cl:17])[C:6]([OH:8])=[O:7])#[N:4]>CO.C(=O)(O)[O-].[Na+]>[C:3]([CH:5]([CH2:9][C:10]1[C:11]([Cl:17])=[CH:12][CH:13]=[CH:14][C:15]=1[Cl:16])[C:6]([OH:8])=[O:7])#[N:4]

참가 물질

5

반응물 2

HCID 4311764Sodium borohydrideHCID 545137902-Cyano-3-(2,6-dichlorophenyl)acrylic acid

생성물 1

HCID 135607172-Cyano 3-(2,6-dichlorophenyl)propanoic acid수율 100.6%

시약·촉매·용매 2

HCID 887Methanol용매HCID 516892Sodium Bicarbonate용매

반응 조건

온도
0 °C

실험 절차

Sodium borohydride (1121 mmol, 42.4 g) was added, in portions over a period of 45 minutes, to a stirred suspension of 2-cyano-3-(2,6-dichlorophenyl)acrylic acid (448 mmol, 108.5 g) in MeOH (1 L) and aqueous saturated sodium bicarbonate (500 mL) at 0° C. After stirring at 0° C. for 30 minutes the cooling bath was removed and the reaction was allowed to warm to room temperature. Stirring was continued at room temperature for 3 hours and the reaction mixture was then left to stand overnight. The reaction mixture was partially concentrated under reduced pressure and the remaining aqueous was diluted with water and then acidified with 5 N HCl. Extraction with ether followed by drying over sodium sulfate, filtering and concentrating under reduced pressure afforded 110 g of 2-cyano-3-(2,6-dichlorophenyl)propanoic acid (100% yield).

후처리

  1. customwas removed
  2. temperatureto warm to room temperature
  3. stirringStirring
  4. waitwas continued at room temperature for 3 hours
  5. waitthe reaction mixture was then left
  6. waitto stand overnight
  7. concentrationThe reaction mixture was partially concentrated under reduced pressure
  8. additionthe remaining aqueous was diluted with water
  9. extractionExtraction with ether
  10. dry with materialby drying over sodium sulfate
  11. filtrationfiltering
  12. concentrationconcentrating under reduced pressure

출처 및 근거

ORD 기록
ord-0dd3e07cd54d4a8881c264bf6c45c76e
출처 데이터셋
uspto-grants-2014_05
특허 번호
US08729274B2

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