Hydrochloric Acid → 3-(But-3-enyloxy)cyclooct-1-yne

HRID 1037696Notes

Reaction equation

Br[C:2]1=[CH:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH:9]1[O:10][CH2:11][CH2:12][CH:13]=[CH2:14].C1CCN2C(=NCCC2)CC1.CCOC(C)=O.Cl>CS(C)=O>[CH2:11]([O:10][CH:9]1[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][C:3]#[C:2]1)[CH2:12][CH:13]=[CH2:14]

Participants

Conditions

Temperature: 60 °C

Procedure

The compound 2 (2.04 g, 7.8 mmol) is dissolved in anhydrous DMSO (10 ml) and heated to 60° C. DBU (2.3 ml, 2 eq.) is added and the solution is stirred for 15 min. before adding further DBU (4.6 ml, 4 eq.) and again stirring for 15 min. Finally, DBU (4.6 ml, 4 eq.) is added a final time and the solution is stirred at 60° C. overnight and subsequently left to return to ambient temperature. 150 ml of AcOEt are added to this solution and extraction is carried out with HCl (1M). When the pH becomes basic, the organic phase is washed with water to neutrality. The extracted phase is dried over MgSO4, filtered and purified by flash chromatography (cyclohexane/AcOEt 99:1) in order to produce the compound 3 (1.22 g, 6.8 mmol, 87%), a colorless liquid.

Workup

stirringagain stirring for 15 min
stirringthe solution is stirred at 60° C. overnight
waitsubsequently left
customto return to ambient temperature
washthe organic phase is washed with water to neutrality
dry with materialThe extracted phase is dried over MgSO4
filtrationfiltered
custompurified by flash chromatography (cyclohexane/AcOEt 99:1) in order

Sources & evidence

ORD record: ord-8341a08d441a4daa800ca74bf3ae3d60
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08546598B2

Reaction notes

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