Sodium borohydride → 2,2-Difluoro-2-(pyridin-2-YL)ethanol

HRID 398363노트

반응식

HRID 398363 반응식
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]([F:14])([F:13])[C:8](OCC)=[O:9].[BH4-].[Na+]>CO>[F:14][C:7]([F:13])([C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=1)[CH2:8][OH:9]

참가 물질

4

반응물 2

HCID 4311764Sodium borohydrideHCID 10631894Ethyl difluoro(pyridin-2-yl)acetate

생성물 1

HCID 99422162,2-Difluoro-2-(pyridin-2-YL)ethanol수율 94.7%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

To a 0° C. stirred solution of 3.97 g (19.7 mmol) of ethyl 2-pyridyldifluoroacetate (prepared according to T. Taguchi, et al., Tetrahedron Lett. 1986, 27, 6103) in 40 mL of methanol was added 757 mg (20 mmol) of sodium borohydride in several portions. After stirring for 0.5 h, the cold bath was removed, and stirring continued another 0.5 h. The reaction was quenched with 2M HCl, and the solvents removed under reduced pressure. The residue was partitioned between ether and 10% Na2CO3, the aqueous layer extracted with several portions of ether and the combined organic layers washed with brine, dried over MgSO4 and the solvents removed to give 2.97 g of a yellow oil that was chromatographed on 65 g of fine SiO2 using 99:1 to 97:3 CH2—Cl2-CH3OH to give the title compound as an almost colorless solid:

후처리

  1. customthe cold bath was removed
  2. stirringstirring
  3. waitcontinued another 0.5 h
  4. customThe reaction was quenched with 2M HCl
  5. customthe solvents removed under reduced pressure
  6. customThe residue was partitioned between ether and 10% Na2CO3
  7. extractionthe aqueous layer extracted with several portions of ether
  8. washthe combined organic layers washed with brine
  9. dry with materialdried over MgSO4
  10. customthe solvents removed

출처 및 근거

ORD 기록
ord-fbb7bc7d9a0c4de29ad245df296d9c27
출처 데이터셋
uspto-grants-2003_08
특허 번호
US06610692B1

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