Borane;tetrahydrofuran → Methyl 2',5'-difluoro-4-(hydroxymethyl)-1,1'-biphenyl-2-carboxylate

HRID 1662547노트

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HRID 1662547 반응식
[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[C:9]1[CH:14]=[CH:13][C:12]([C:15](O)=[O:16])=[CH:11][C:10]=1[C:18]([O:20][CH3:21])=[O:19].B.C1COCC1>C1COCC1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[C:9]1[C:10]([C:18]([O:20][CH3:21])=[O:19])=[CH:11][C:12]([CH2:15][OH:16])=[CH:13][CH:14]=1

참가 물질

4

반응물 2

HCID 2723981Borane;tetrahydrofuranHCID 577063522',5'-Difluoro-2-((methyloxy)carbonyl)-1,1'-biphenyl-4-carboxylic acid

생성물 1

HCID 57705744Methyl 2',5'-difluoro-4-(hydroxymethyl)-1,1'-biphenyl-2-carboxylate수율 87.2%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
23 °C

실험 절차

To a stirred solution of 83.27B (0.585 g, 2 mmol) in THF (20 mL) at 0° C. was added borane-THF (4 mL, 4 mmol, 1.0M). The reaction was warmed to 23° C. and stirring was continued for four hours. The reaction mixture was then concentrated in vacuo. The reaction was diluted with 1N HCl and extracted three times with EtOAc. After drying over anhydrous magnesium sulfate and filtering, the organic solvent was removed under reduced pressure and the product was then purified on silica gel (0-40% EtOAc in hexanes) to yield 83.27C as a colorless oil (0.485 g, 87% yield).

후처리

  1. concentrationThe reaction mixture was then concentrated in vacuo
  2. additionThe reaction was diluted with 1N HCl
  3. extractionextracted three times with EtOAc
  4. dry with materialAfter drying over anhydrous magnesium sulfate
  5. filtrationfiltering
  6. customthe organic solvent was removed under reduced pressure
  7. customthe product was then purified on silica gel (0-40% EtOAc in hexanes)

출처 및 근거

ORD 기록
ord-aeb38961863b495ab85acacef7ab0fea
출처 데이터셋
uspto-grants-2011_10
특허 번호
US08030354B2

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