Sodium Hydroxide → HCID 178436259, compound

HRID 370676Notes

Reaction equation

HRID 370676 reaction equation
Br[C:2](Br)=[CH:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][C@H:12]2[CH2:17][CH2:16][C@H:15]([CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[CH2:14][CH2:13]2)=[CH:6][CH:5]=1.C([Li])CCC.[OH-].[Na+]>O1CCCC1.CCCCCC>[C:3]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][C@H:12]2[CH2:13][CH2:14][C@H:15]([CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[CH2:16][CH2:17]2)=[CH:6][CH:5]=1)#[CH:2]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 178418339ButyllithiumHCID 178444401HCID 178444401, compound

Product 1

HCID 178436259HCID 178436259, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

In an analogous manner to Example 5, a solution of β,β-dibromo-p-[2-(trans-4-pentylcyclohexyl)ethyl]styrene in absolute tetrahydrofuran was placed in a sulphonation flask and treated within 5 minutes with a solution of butyl lithium in hexane. After completion of the addition, the mixture was stirred at the same temperature for a further 90 minutes, then poured into 1N sodium hydroxide and extracted with petroleum ether. The organic phases were washed with water and saturated sodium chloride solution, dried over magnesium sulphate and concentrated. Low-pressure chromatography of the residue on silica gel with hexane gave pure 1-ethynyl-4-[2-(trans-4-pentylcyclohexyl)ethyl]benzene as colourless crystals; m.p. (C-N) 25.5° C., cl.p. 42.5° C.

Workup

  1. additionAfter completion of the addition
  2. extractionextracted with petroleum ether
  3. washThe organic phases were washed with water and saturated sodium chloride solution
  4. dry with materialdried over magnesium sulphate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-a65fd892bdc84555adc30772a17fac9e
Source dataset
uspto-grants-1985_07
Patent number
US04528114

Reaction notes

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