Water → HCID 178455713, compound

HRID 370686Notes

Reaction equation

HRID 370686 reaction equation
Br[C:2](Br)=[CH:3][C@H:4]1[CH2:9][CH2:8][C@H:7]([C:10]2[CH:15]=[CH:14][C:13]([CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])=[CH:12][CH:11]=2)[CH2:6][CH2:5]1.C([Li])CCC.O>O1CCCC1.CCCCCC>[C:3]([C@H:4]1[CH2:5][CH2:6][C@H:7]([C:10]2[CH:15]=[CH:14][C:13]([CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])=[CH:12][CH:11]=2)[CH2:8][CH2:9]1)#[CH:2]

Participants

6

Reactant 3

HCID 962WaterHCID 178418339ButyllithiumHCID 178442146HCID 178442146, compound

Product 1

HCID 178455713HCID 178455713, compoundYield 86.5%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Conditions

Temperature
-78 °C

Procedure

A solution of 480 mg of 1-[trans-4-(2,2-dibromovinyl)cyclohexyl]-4-pentylbenzene in 60 ml of absolute tetrahydrofuran was placed at -78° C. in a sulphonation flask under argon gasification and treated within 3 minutes with 3.2 ml of a 0.1N solution of butyl lithium in hexane. After completion of the addition, the mixture was stirred at -78° C. for a further 2.5 hours, then poured into 150 ml of water and extracted three times with 150 ml of petroleum ether each time. The organic phases were washed with 100 ml of water, dried over magnesium sulphate and concentrated. Low-pressure chromatography (0.5 bar) of the residue (310 mg) on silica gel with hexane gave 255 mg (83.5%) of 1-(trans-4-ethynylcyclohexyl)-4-pentylbenzene as a colourless oil (purity 95.9%).

Workup

  1. additionAfter completion of the addition
  2. extractionextracted three times with 150 ml of petroleum ether each time
  3. washThe organic phases were washed with 100 ml of water
  4. dry with materialdried over magnesium sulphate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-c76d4a901dcf4a37919c966c1a60365e
Source dataset
uspto-grants-1985_07
Patent number
US04528114

Reaction notes

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