Methanol → HCID 86730205, 화합물

HRID 57451노트

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HRID 57451 반응식
[Cl:1][C:2]1[C:3]([C:13]([F:16])([F:15])[CH3:14])=[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[C:13]([F:15])([F:16])[CH3:14]

참가 물질

5

반응물 3

HCID 887MethanolHCID 4148881Lithium borohydrideHCID 86730206Ethyl 5-chloro-6-(1,1-difluoroethyl)nicotinate

생성물 1

HCID 86730205HCID 86730205, 화합물수율 95.1%

시약·촉매·용매 1

HCID 3283Diethyl Ether용매

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온도
40 °C

실험 절차

To a solution of ethyl 5-chloro-6-(1,1-difluoroethyl)nicotinate (2.68 g, 10.74 mmol) in Et2O (40 mL) was added LiBH4 (0.351 g, 16.10 mmol), followed by dropwise addition of methanol (0.653 mL, 16.10 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 (3×50 mL). The organic was then dried (Na2SO4) and concentrated under reduced pressure to give final crude product (2.12 g). LCMS m/z 208.0 (M+H)+, Rt 0.63 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 (3×50 mL)
  5. dry with materialThe organic was then dried (Na2SO4)
  6. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-ec68920441b04f92af4b5a87376574ac
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09434719B2

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