Hydrochloric Acid → 4-{2-[3,4-Bis(difluoromethoxy)phenyl]-2-{6-[4-(trifluoromethoxy)phenoxy]-3-pyridyl}ethyl}pyridine

HRID 567947노트

반응식

HRID 567947 반응식
C([CH:6]([C:40]1[CH:45]=[CH:44][N:43]=[CH:42][CH:41]=1)[CH:7]([C:26]1[CH:31]=[CH:30][C:29]([O:32][CH:33]([F:35])[F:34])=[C:28]([O:36][CH:37]([F:39])[F:38])[CH:27]=1)[C:8]1[CH:9]=[N:10][C:11]([O:14][C:15]2[CH:20]=[CH:19][C:18]([O:21][C:22]([F:25])([F:24])[F:23])=[CH:17][CH:16]=2)=[CH:12][CH:13]=1)(OCC)=O.C1COCC1.[Li+].[OH-].Cl>O.CO>[F:39][CH:37]([F:38])[O:36][C:28]1[CH:27]=[C:26]([CH:7]([C:8]2[CH:9]=[N:10][C:11]([O:14][C:15]3[CH:20]=[CH:19][C:18]([O:21][C:22]([F:25])([F:24])[F:23])=[CH:17][CH:16]=3)=[CH:12][CH:13]=2)[CH2:6][C:40]2[CH:45]=[CH:44][N:43]=[CH:42][CH:41]=2)[CH:31]=[CH:30][C:29]=1[O:32][CH:33]([F:35])[F:34]

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 212628244-{1-Carbethoxy-2-[3,4-bis(difluoromethoxy)phenyl]-2-{6-[4-(trifluoromethoxy)phenoxy]-3-pyridyl}ethyl}pyridine

생성물 1

HCID 212627884-{2-[3,4-Bis(difluoromethoxy)phenyl]-2-{6-[4-(trifluoromethoxy)phenoxy]-3-pyridyl}ethyl}pyridine

시약·촉매·용매 2

HCID 887Methanol용매HCID 962Water용매

반응 조건

온도
65 °C

실험 절차

To a solution of the crude ester from Step 4 above in 25 mL of a 3:1:1 mixture of THF:MeOH:water, was added 5.1 mL (10.3 mmol) of a 2 N solution of LiOH. The resulting solution was stirred at 65° C. for 1.5 h, cooled down to room temperature followed by the addition of 10 mL of a 1.0 N HCl solution. The resulting mixture was rotovaped down to evaporate MeOH and the aqueous residue was diluted with ethyl acetate. The organic layer was washed with water and brine, dried over MgSO4 and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel (50% Ethyl acetate/hexane) to afford the desired pyridine as an oil (380 mg, 68% from Step 2).

후처리

  1. temperaturecooled down to room temperature
  2. customto evaporate MeOH
  3. additionthe aqueous residue was diluted with ethyl acetate
  4. washThe organic layer was washed with water and brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by flash chromatography on silica gel (50% Ethyl acetate/hexane)
  8. customto afford the desired pyridine as an oil (380 mg, 68% from Step 2)

출처 및 근거

ORD 기록
ord-a2fbb9c7d1604bdea08a9453bafcd429
출처 데이터셋
uspto-grants-2001_01
특허 번호
US06180650B2

반응 노트

불러오는 중…