1-Bromohexane → HCID 21954826, compound

HRID 1011838Notes

Reaction equation

HRID 1011838 reaction equation
C([Li])CCC.[C:6]([C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:11]=[CH:10][CH:9]=1)#[CH:7].CC(C)([O-])C.[K+].Br[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30]>O.O1CCCC1.CCCCCC>[C:6]([C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:11]=[CH:10][C:9]=1[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])#[CH:7]

Participants

8

Reactant 4

HCID 81011-BromohexaneHCID 1233571-EthynylnaphthaleneHCID 23665647Potassium tert-butoxideHCID 178418339Butyllithium

Product 1

HCID 21954826HCID 21954826, compoundYield 47.2%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Conditions

Temperature
-90 °C

Procedure

Under a nitrogen atmosphere at −50° C., 1.6 mol/l hexane solution of n-butyllithium was added to 30 ml of a tetrahydrofuran solution containing 3 g of ethynylnaphthalene. After cooling to −90° C., 15 ml of a tetrahydrofuran solution containing 2.5 g of potassium tertiary butoxide was added thereto, and the mixture was stirred at −80° C. for 1 hour and then allowed to warm to 5° C. 3.3 g of bromohexane was added dropwise at −70° C., and the mixture was stirred at 30° C. overnight. 100 ml of water was added dropwise at 0° C., and the compounds generated were extracted with added hexane. The hexane layer was washed thrice with 300 ml of distilled water and dried over anhydrous magnesium sulfate for 24 hours, and the mixture was then filtered and evaporated for removal of the solvent. After column purification and solvent removal, the product was purified by column chromatography while hexane was used as the developing solvent, to give 2.2 g of 1-ethynyl-2-n-hexylnaphthalene.

Workup

  1. additionwas added
  2. temperatureto warm to 5° C
  3. stirringthe mixture was stirred at 30° C. overnight
  4. extractionthe compounds generated were extracted with added hexane
  5. washThe hexane layer was washed thrice with 300 ml of distilled water
  6. dry with materialdried over anhydrous magnesium sulfate for 24 hours
  7. filtrationthe mixture was then filtered
  8. customevaporated for removal of the solvent
  9. customAfter column purification and solvent removal
  10. customthe product was purified by column chromatography while hexane

Sources & evidence

ORD record
ord-4b2a3c0c3f4947da864c1ab94e5e9795
Source dataset
uspto-grants-2011_07
Patent number
US07977441B2

Reaction notes

Loading…