Water → HCID 178436318, compound

HRID 370670Notes

Reaction equation

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

Participants

Conditions

Temperature: -10 °C

Procedure

A solution of 7.88 g of β,β-dibromo-p-(trans-4-pentylcyclohexyl)styrene in 150 ml of absolute tetrahydrofuran was placed at -78° C. in a sulphonation flask under argon gasification and treated within 10 minutes with 63 ml of a 1.2N solution of butyl lithium in hexane. After completion of the addition, the mixture was stirred at -78° C. for a further 1 hour and at -10° C. for 1 hour, then poured into 100 ml of water and extracted three times with 100 ml of petroleum ether each time. The organic phases were washed with 100 ml of water and with 100 ml of saturated sodium chloride solution, dried over magnesium sulphate and concentrated. Low-pressure chromatography (0.5 bar) of the residual crystallizing oil on silica gel with hexane gave 4.13 g (85%) of 1-ethynyl-4-(trans-4-pentylcyclohexyl)benzene as colourless crystals (purity 99.3%); m.p. (C-N) 39.4° C., cl.p. 42.1° C.

Workup

additionAfter completion of the addition
extractionextracted three times with 100 ml of petroleum ether each time
washThe organic phases were washed with 100 ml of water and with 100 ml of saturated sodium chloride solution
dry with materialdried over magnesium sulphate
concentrationconcentrated
customLow-pressure chromatography (0.5 bar) of the residual crystallizing oil on silica gel with hexane

Sources & evidence

ORD record: ord-7ca88543785d4284ad425c5ecb77925f
Source dataset: uspto-grants-1985_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04528114

Reaction notes

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