3,4-dihydro-2H-pyran → 2-(4-bromo-3-fluorophenoxy)tetrahydro-2H-pyran

HRID 84240

反応式

HRID 84240 の反応式
C1(C)C=CC(S(O)(=O)=O)=CC=1.[NH+]1C=CC=CC=1.[Br:18][C:19]1[CH:24]=[CH:23][C:22]([OH:25])=[CH:21][C:20]=1[F:26].[O:27]1[CH:32]=[CH:31][CH2:30][CH2:29][CH2:28]1.CCOC(C)=O>ClCCl.CCCCCCC>[Br:18][C:19]1[CH:24]=[CH:23][C:22]([O:25][CH:28]2[CH2:29][CH2:30][CH2:31][CH2:32][O:27]2)=[CH:21][C:20]=1[F:26]

参加物

7

反応物 4

HCID 80803,4-dihydro-2H-pyranHCID 8857Ethyl AcetateHCID 27791534-Bromo-3-fluorophenolHCID 22033616Pyridinium.p-toluenesulfonate

生成物 1

HCID 587212402-(4-bromo-3-fluorophenoxy)tetrahydro-2H-pyran収率 33%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 8900Heptane溶媒

実験手順

Pyridinium p-toluene sulfonic acid (789 mg, 3.1 mmol) was added to a solution of 4-bromo-3-fluorophenol (4.00 g, 20.9 mmol) and 3,4-dihydro-2H-pyran (3.52 g, 41.9 mmol) in dichloromethane (105 mL, 0.2M). After 2h the reaction was quenched with saturated aqueous sodium bicarbonate and the layers were separated. The aqueous layer was extracted with dichloromethane (2×). The organic layers were combined, dried (Na2SO4), filtered and concentrated to give a colorless oil. The material was loaded onto a 25g silica guard column and run on a 330g column with 0-5% EtOAc in heptane. Desired material was concentrated down yielding 1900 mg (33%) of a clear colorless oil.

後処理

  1. customAfter 2h the reaction was quenched with saturated aqueous sodium bicarbonate
  2. customthe layers were separated
  3. extractionThe aqueous layer was extracted with dichloromethane (2×)
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give a colorless oil
  8. concentrationDesired material was concentrated

出典と根拠

ORDレコード
ord-83d120aea195445e9ecc505c8ba48087
出典データセット
uspto-grants-2014_09
特許番号
US08846933B2

関連ノート

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