Water → 3-(Benzylsulfanyl)-2-methylfuran

HRID 436184

反応式

HRID 436184 の反応式
C[O-].[Na+].[CH3:4][C:5]1[O:6][CH:7]=[CH:8][C:9]=1[SH:10].[CH2:11](Br)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.O>CO.Cl.CCCCCC>[CH2:11]([S:10][C:9]1[CH:8]=[CH:7][O:6][C:5]=1[CH3:4])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

参加物

8

反応物 4

HCID 962WaterHCID 7498Benzyl BromideHCID 342862-Methyl-3-furanthiolHCID 10942334Sodium Methoxide

生成物 1

HCID 215030903-(Benzylsulfanyl)-2-methylfuran

試薬・触媒・溶媒 3

HCID 313Hydrochloric Acid触媒HCID 887Methanol溶媒3 回HCID 8058Hexane溶媒

実験手順

Into a 25 ml round bottom flask equpped with magnetic stirrer, thermometer, reflux condenser and heating mantle is placed a solution containing 0.27 g (0.005 moles) of sodium methoxide in 3 ml of absolute methanol. With stirring and while maintaining the temperature at 25° C-30° C, 0.57 g (0.005 moles) of 2-methyl-3-furan thiol in 3 ml absolute methanol is added. The reaction mass is stirred for a period of 10 minutes. 0.86 g of benzyl bromide dissolved in 2 ml absolute methanol is then added to the reaction mass with stirring at 25° C. The reaction mass is heated to reflux (50° C-60° C) and maintained at this temperature with stirring for a period of 4 hours. The reaction mass is then allowed to cool down to room temperature and is admixed with 10 ml of water with stirring. The reaction mass is neutralized to a pH of 5-6 with one drop of 10% hydrochloric acid and 5 ml hexane is added with stirring. The mass is then transferred to a separatory funnel and the organic and aqueous phases are separated. The aqueous phase is diluted with 5 ml water and extracted with 7 ml of n-hexne. The hexane extracts are combined, washed with 5 ml saturated sodium chloride, dried over anhydrous sodium sulfate, and gravity filtered. The resulting solution is then concentrated to an amber oil using rotary evaporation under a water aspirator vacuum. NMR, IR and Mass Spectral analyses confirm that the major product isolated by GLC trapping has the structure: ##STR32##

後処理

  1. customInto a 25 ml round bottom flask equpped with magnetic stirrer
  2. temperaturethermometer, reflux condenser
  3. temperatureheating mantle
  4. temperaturewhile maintaining the temperature at 25° C-30° C
  5. stirringThe reaction mass is stirred for a period of 10 minutes
  6. additionis then added to the reaction mass
  7. stirringwith stirring at 25° C
  8. temperatureThe reaction mass is heated
  9. temperatureto reflux (50° C-60° C)
  10. temperaturemaintained at this temperature
  11. stirringwith stirring for a period of 4 hours
  12. stirringwith stirring
  13. additionis added
  14. stirringwith stirring
  15. customThe mass is then transferred to a separatory funnel
  16. customthe organic and aqueous phases are separated
  17. additionThe aqueous phase is diluted with 5 ml water
  18. extractionextracted with 7 ml of n-hexne
  19. washwashed with 5 ml saturated sodium chloride
  20. dry with materialdried over anhydrous sodium sulfate, and gravity
  21. filtrationfiltered
  22. concentrationThe resulting solution is then concentrated to an amber oil
  23. customevaporation under a water
  24. customisolated by GLC trapping

出典と根拠

ORDレコード
ord-3129b7153018464880e68b8b97b1df2c
出典データセット
uspto-grants-1977_02
特許番号
US04007287

関連ノート

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