Methanol → 3-Pyridinemethanol, 5-chloro-6-(2,2,2-trifluoroethoxy)-

HRID 57453노트

반응식

HRID 57453 반응식
[Cl:1][C:2]1[C:3]([O:13][CH2:14][C:15]([F:18])([F:17])[F:16])=[N:4][CH:5]=[C:6]([CH:12]=1)[C:7](OCC)=[O:8].[Li+].[BH4-].CO>CCOCC>[Cl:1][C:2]1[CH:12]=[C:6]([CH2:7][OH:8])[CH:5]=[N:4][C:3]=1[O:13][CH2:14][C:15]([F:16])([F:17])[F:18]

참가 물질

5

반응물 3

HCID 887MethanolHCID 4148881Lithium borohydrideHCID 86730207Ethyl 5-chloro-6-(2,2,2-trifluoroethoxy)nicotinate

생성물 1

HCID 612563313-Pyridinemethanol, 5-chloro-6-(2,2,2-trifluoroethoxy)-수율 98.6%

시약·촉매·용매 1

HCID 3283Diethyl Ether용매

반응 조건

온도
40 °C

실험 절차

To a solution of ethyl 5-chloro-6-(2,2,2-trifluoroethoxyl)nicotinate (7.51 g, 26.5 mmol) in Et2O (200 mL) was added LiBH4 (0.865 g, 39.7 mmol), followed by drop wise addition of methanol (1.611 ml, 39.7 mmol). The reaction was refluxed at 40° C. for one hour. The reaction mixture was then cooled to 0° C., and quenched with HCl (1M) until pH=2 for aqueous layer. The phases were separated and the aqueous layer was extracted with DCM (3×200 mL). The organic was then dried (Na2SO4) and concentrated under reduced pressure to give final crude product (6.31 g). LCMS m/z 242.1 (M+H)+, Rt 0.77 min.

후처리

  1. temperatureThe reaction mixture was then cooled to 0° C.
  2. customquenched with HCl (1M) until pH=2 for aqueous layer
  3. customThe phases were separated
  4. extractionthe aqueous layer was extracted with DCM (3×200 mL)
  5. dry with materialThe organic was then dried (Na2SO4)
  6. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-b3d4231668e745cbb8597b58c6a8beeb
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09434719B2

반응 노트

불러오는 중…