Acetic Acid → 3-Fluoro-2-vinyl-isonicotinic acid methyl ester

HRID 1426285노트

반응식

HRID 1426285 반응식
[F:1][C:2]1[C:10]([CH:11]=[CH2:12])=[N:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[CH3:13][Si](C=[N+]=[N-])(C)C.CCOCC.C(O)(=O)C>CO>[F:1][C:2]1[C:10]([CH:11]=[CH2:12])=[N:9][CH:8]=[CH:7][C:3]=1[C:4]([O:6][CH3:13])=[O:5]

참가 물질

6

반응물 4

HCID 176Acetic AcidHCID 3283Diethyl EtherHCID 167693TrimethylsilyldiazomethaneHCID 696734763-Fluoro-2-vinylisonicotinic acid

생성물 1

HCID 696727743-Fluoro-2-vinyl-isonicotinic acid methyl ester

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

To a solution of 3-fluoro-2-vinylisonicotinic acid (1.3 g, 7.8 mmol, from Step 1) in methanol (20 mL) cooled to 0° C., was added dropwise 2.0M trimethylsilyldiazomethane in ether (21.6 mL, 44 mmol). When the reaction was complete, acetic acid was added dropwise to quench excess reagent and the volume of solvent was reduced in vacuo. The mixture was partitioned between saturated sodium bicarbonate solution and DCM. The aqueous portion was extracted with a total of three portions of DCM. The combined extracts were dried over sodium sulfate, decanted and concentrated and The product was used without further purification (1.4 g, 100%). 1H NMR (300 MHz, CDCl3): δ 8.47 (d, 1H), 7.62 (dd, 1H), 7.08 (ddd, 1H), 6.48 (dd, 1H), 5.65 (dd, 1H), 3.97 (s, 3H); LCMS (M+H)+: 182.0.

후처리

  1. customto quench excess reagent
  2. customThe mixture was partitioned between saturated sodium bicarbonate solution and DCM
  3. extractionThe aqueous portion was extracted with a total of three portions of DCM
  4. dry with materialThe combined extracts were dried over sodium sulfate
  5. customdecanted
  6. concentrationconcentrated
  7. customThe product was used without further purification (1.4 g, 100%)

출처 및 근거

ORD 기록
ord-bfc661d6c6d44221bf7e79961084d0e6
출처 데이터셋
uspto-grants-2015_01
특허 번호
US08933085B2

반응 노트

불러오는 중…