Sodium hydride → HCID 178450575, compound

HRID 726448Notes

Reaction equation

HRID 726448 reaction equation
[CH2:1]([C@H:4]1[CH2:9][CH2:8][C@H:7]([C@H:10]2[CH2:15][CH2:14][C@H:13]([C@H:16]3[CH2:21][CH2:20][C@H:19]([OH:22])[CH2:18][CH2:17]3)[CH2:12][CH2:11]2)[CH2:6][CH2:5]1)[CH2:2][CH3:3].[H-].[Na+].Br[CH2:26][CH:27]=[CH:28][CH3:29]>CN(C=O)C>[CH2:26]([O:22][C@H:19]1[CH2:18][CH2:17][C@H:16]([C@H:13]2[CH2:14][CH2:15][C@H:10]([C@H:7]3[CH2:6][CH2:5][C@H:4]([CH2:1][CH2:2][CH3:3])[CH2:9][CH2:8]3)[CH2:11][CH2:12]2)[CH2:21][CH2:20]1)[CH:27]=[CH:28][CH3:29]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 1224142-Butene, 1-bromo-HCID 178448067HCID 178448067, compound

Product 1

HCID 178450575HCID 178450575, compoundYield 49.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

To a solution of 10.0 g (33.1 mmol) of trans-4-(trans-4-(trans-4-propylcyclohexyl)cyclohexyl)cyclohexanol in 100 ml of DMF was added dropwise, while stirring the solution at room temperature, a suspension of 1.19 g (49.6 mmol) of NaH in 10 ml of DMF. After completion of the dropwise addition, the reaction mixture was stirred for 2 hours and then the temperature of the reaction mixture was gradually allowed to rise up to about 80° C. and a solution of 5.35 g (39.7 mmol) of 1-bromo-2-butene in 20 ml of DMF was added dropwise. After completion of the dropwise addition, the mixture was heated under reflux at the same temperature for 5 hours. After the reaction solution was allowed to cool down to room temperature, the reaction product was poured into an ice-water and extracted with 500 ml of toluene. The organic layer was washed three times with water, dried over anhydrous magnesium sulfate and the solvent was distilled off under reduced pressure. A silica gel column chromatography (developing solvent: toluene) of the residue gave 5.96 g of crude 1-(2-butenyloxy)-trans-4-(trans-4-(trans-4-propylcyclohexyl)cyclohexyl)cyclohexane.

Workup

  1. additionAfter completion of the dropwise addition
  2. stirringthe reaction mixture was stirred for 2 hours
  3. customto rise up to about 80° C.
  4. additionAfter completion of the dropwise addition
  5. temperaturethe mixture was heated
  6. temperatureunder reflux at the same temperature for 5 hours
  7. temperatureto cool down to room temperature
  8. extractionextracted with 500 ml of toluene
  9. washThe organic layer was washed three times with water
  10. dry with materialdried over anhydrous magnesium sulfate
  11. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-6a21a4a0a9894f28911d27993d599338
Source dataset
uspto-grants-1998_01
Patent number
US05709820

Reaction notes

Loading…