Lithium borohydride → 2-(4-Bromo-2-methyl-phenyl)-4-hydroxy-butyronitrile

HRID 503908노트

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HRID 503908 반응식
[BH4-].[Li+].C[O:4][C:5](=O)[CH2:6][CH:7]([C:10]1[CH:15]=[CH:14][C:13]([Br:16])=[CH:12][C:11]=1[CH3:17])[C:8]#[N:9].OS([O-])(=O)=O.[K+].[O-]S([O-])(=O)=O.[Na+].[Na+]>C1COCC1>[Br:16][C:13]1[CH:14]=[CH:15][C:10]([CH:7]([CH2:6][CH2:5][OH:4])[C:8]#[N:9])=[C:11]([CH3:17])[CH:12]=1

참가 물질

5

반응물 3

HCID 4148881Lithium borohydrideHCID 668771313-(4-Bromo-2-methyl-phenyl)-3-cyano-propionic acid methyl esterHCID 86586342KHSO4 Na2SO4

생성물 1

HCID 594283342-(4-Bromo-2-methyl-phenyl)-4-hydroxy-butyronitrile수율 87%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
0 °C

실험 절차

Lithium borohydride (4.99 g, 0.2290 mol) was added to a room temperature solution of 3-(4-bromo-2-methyl-phenyl)-3-cyano-propionic acid methyl ester (43.08 g, 0.1527 mol) in THF (500 mL) and the reaction mixture was stirred overnight. The reaction mixture was cooled to 0° C., and a solution of 10% KHSO4/Na2SO4 was slowly added until pH 1-2 was reached. The resulting mixture was extracted with EtOAc, and the combined organic extracts were washed with water and brine, dried over Na2SO4, filtered, and evaporated under reduced pressure. The residue was purified via flash chromatography (hexane/EtOAc, 7/3) to give 27.3 g (87% yield) of 2-(4-bromo-2-methyl-phenyl)-4-hydroxy-butyronitrile as a white solid.

후처리

  1. extractionThe resulting mixture was extracted with EtOAc
  2. washthe combined organic extracts were washed with water and brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customevaporated under reduced pressure
  6. customThe residue was purified via flash chromatography (hexane/EtOAc, 7/3)

출처 및 근거

ORD 기록
ord-9e7375483a8e47399aedbb2bb604d1d2
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07776910B2

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