Benzyl Bromide → HCID 67282870, 화합물

HRID 1187478노트

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HRID 1187478 반응식
[OH-].[Na+].[OH:3][C:4]1[C:9](=[O:10])[CH:8]=[CH:7][N:6]([CH3:11])[C:5]=1[CH:12]([OH:17])[C:13]([F:16])([F:15])[F:14].[CH2:18](Br)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>O.CO>[CH2:18]([O:3][C:4]1[C:9](=[O:10])[CH:8]=[CH:7][N:6]([CH3:11])[C:5]=1[CH:12]([OH:17])[C:13]([F:16])([F:14])[F:15])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

참가 물질

6

반응물 3

HCID 7498Benzyl BromideHCID 14798Sodium HydroxideHCID 67282261HCID 67282261, 화합물

생성물 1

HCID 67282870HCID 67282870, 화합물수율 31.7%

시약·촉매·용매 2

HCID 887Methanol용매HCID 962Water용매

실험 절차

A solution of NaOH (1.77 g dissolved in 20 mL, 44.4 mmol) in de-ionized water was added dropwise to a suspension of 3-hydroxy-1-methyl-2-(2,2,2-trifluoro-1-hydroxy-ethyl)-1H-pyridin-4-one (9.00 g, 40.3 mmol) in methanol (100 mL), and followed by benzyl bromide (5.28 mL, 44.4 mmol) at room temperature. The resulting suspension was refluxed for 3.5 h, and then stirred at RT for overnight. Methanol was removed under vacuum using the rotary evaporator, and the residue was diluted with water and extracted two times with CH2Cl2 (2×100 mL). The combined organic fractions were washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated to dryness. The residue was purified by flash column chromatography on silica gel using a mixture of methanol and ethyl acetate (10/90, v/v) as eluant. Fractions rich in the product were pooled together and evaporated to dryness to give 4 g of 3-benzyloxy-1-methyl-2-(2,2,2-trifluoro-1-hydroxy-ethyl)-1H-pyridin-4-one as a solid.

후처리

  1. temperatureThe resulting suspension was refluxed for 3.5 h
  2. customMethanol was removed under vacuum
  3. customthe rotary evaporator
  4. additionthe residue was diluted with water
  5. extractionextracted two times with CH2Cl2 (2×100 mL)
  6. washThe combined organic fractions were washed with brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated to dryness
  10. customThe residue was purified by flash column chromatography on silica gel using
  11. additiona mixture of methanol and ethyl acetate (10/90
  12. customevaporated to dryness

출처 및 근거

ORD 기록
ord-e11a9904b65d4f3a97efb856dad4a9dd
출처 데이터셋
uspto-grants-2014_03
특허 번호
US08673943B2

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