Tetrahydrofuran → HCID 68790321, compound

HRID 2093124Notes

Reaction equation

HRID 2093124 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][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28]>ClCCl.O>[CH2:28]([O:8][CH2:7][CH2:6][C:2]1[S:1][CH:5]=[CH:4][CH:3]=1)[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH3:17]

Participants

7

Conditions

Temperature
0 °C

Procedure

13 g of 2-thiopheneethanol was cooled to 0° C., and to this, a suspension formed by adding 5.8 g of sodium hydride (60% in oil) to 100 ml of tetrahydrofuran was added dropwise. The solution was stirred at 0° C. for 20 minutes under a nitrogen atmosphere, and to this, 25 g of 1-bromododecane was added dropwise. The resulting solution was heated to 90° C. and stirred for 11.5 hours. 100 ml of water and 150 ml of dichloromethane 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 16 g of 2-(2-dodecyloxyethyl)thiophene.

Workup

  1. customto this, a suspension formed
  2. additionwas added dropwise
  3. temperatureThe resulting solution was heated to 90° C.
  4. stirringstirred for 11.5 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-04fe32f8290a4e2b8b34775630c11283
Source dataset
uspto-grants-2013_05
Patent number
US08441002B2

Reaction notes

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