Hexane → HCID 22610225, compound

HRID 1860304Notes

Reaction equation

HRID 1860304 reaction equation
[CH2:1]([Li])[CH2:2][CH2:3][CH3:4].[CH3:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11]>C1COCC1>[C:3]([C:2]1([CH2:1][CH2:8][CH2:7][CH2:6][CH3:11])[CH2:4][C:9]2[C:10]([CH3:10])([CH3:2])[CH2:11][CH2:6][C:7]([CH3:1])([CH3:9])[C:8]=2[CH2:3]1)#[CH:4]

Participants

4

Reactant 2

HCID 8058HexaneHCID 178418339Butyllithium

Product 1

HCID 22610225HCID 22610225, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

0.6 g of this dibromide were dissolved in 10 ml of THF, cooled to −78° C. and treated dropwise with 1.8 ml of a 1.6 molar solution of butyl lithium in hexane. After stirring at −78° C. for 1 hour and at room temperature for 1 hour, the reaction mixture was poured on ice/saturated aqueous ammonium chloride solution and extracted with hexane. The organic phase was dried (Na2SO4) and the solvent evaporated to yield 0.4 g of 2-ethynyl-4,4,7,7-tetramethyl-2-pentyl-2,3,4,5,6,7-hexahydro-1H-indene as yellowish oil.

Workup

  1. additionthe reaction mixture was poured on ice/saturated aqueous ammonium chloride solution
  2. extractionextracted with hexane
  3. dry with materialThe organic phase was dried (Na2SO4)
  4. customthe solvent evaporated

Sources & evidence

ORD record
ord-e9755096b99241688641897b160ced7c
Source dataset
uspto-grants-2003_03
Patent number
US06528677B1

Reaction notes

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