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

HRID 567947ノート

反応式

HRID 567947 の反応式
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]

参加物

7

反応物 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

生成物 1

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

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 962Water溶媒

反応条件

温度
65 °C

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-a2fbb9c7d1604bdea08a9453bafcd429
出典データセット
uspto-grants-2001_01
特許番号
US06180650B2

反応ノート

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