Tetrahydrofuran → HCID 58273767, compound

HRID 2093126Notes

Reaction equation

HRID 2093126 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][CH2:7][OH:8].[H-].[Na+].O1CCCC1.Br[CH2:17][CH2:18][O:19][CH2:20][CH2:21][CH2:22][CH3:23]>CCCCCC.O>[CH2:20]([O:19][CH2:18][CH2:17][O:8][CH2:7][CH2:6][C:2]1[S:1][CH:5]=[CH:4][CH:3]=1)[CH2:21][CH2:22][CH3:23]

Participants

7

Conditions

Temperature
0 °C

Procedure

6.1 g of 2-thiopheneethanol was cooled to 0° C., and to this, a suspension formed by adding 2.8 g of sodium hydride (60% in oil) to 50 ml of tetrahydrofuran was added dropwise. The solution was stirred at 0° C. for 20 minutes under a nitrogen atmosphere, and to this, 8.2 g of 1-(2-bromo-ethoxy)-butane was added dropwise. Thereafter, the solution was heated to 90° C. and stirred for 9 hours. 100 ml of water and 100 ml of hexane were added to the reaction solution to separate the organic layer. The organic layer was washed with 300 ml of water and then dried over anhydrous magnesium sulfate. The resulting solution was concentrated by a rotary evaporator and purified by a column chromatography (filler: silica gel, eluent: hexane/dichloromethane) to obtain 3.5 g of 2-[2-(2-butoxy-ethoxy)ethyl]-thiophene.

Workup

  1. customto this, a suspension formed
  2. additionwas added dropwise
  3. temperatureThereafter, the solution was heated to 90° C.
  4. stirringstirred for 9 hours
  5. customto separate the organic layer
  6. washThe organic layer was washed with 300 ml of water
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationThe resulting solution was concentrated by a rotary evaporator
  9. custompurified by a column chromatography (filler: silica gel, eluent: hexane/dichloromethane)

Sources & evidence

ORD record
ord-a73e88e80135411d86ba75235f95c86e
Source dataset
uspto-grants-2013_05
Patent number
US08441002B2

Reaction notes

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