Iodoethane → HCID 15913958, compound

HRID 1838514Notes

Reaction equation

[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[CH2:10][CH2:11][C:12]1[CH2:13][C:14]2[C:19]([CH:20]=1)=[CH:18][CH:17]=[CH:16][CH:15]=2.[Li][CH2:22][CH2:23]CC.[CH3:26][CH2:27]CCCC.C(I)C>C1COCC1>[CH2:22]([CH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[CH2:10][CH2:11][C:12]1[CH:13]([CH2:26][CH3:27])[C:14]2[C:19]([CH:20]=1)=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH3:23]

Participants

Conditions

Temperature: -10 °C

Procedure

1.36 g, 5.26 mmol of 1,2-bis(2-indenyl)ethane, prepared as described in the above reported Synthesis 1(a), were dissolved in 25 mL THF and cooled to −10° C. 5.5 ml of a 1.6 M solution of BuLi in hexane (8.8 mmoles) were added and the resulting orange/brown solution was stirred for 2 hours, at room temperature. To the obtained mixture was added, by means of a cannula, a solution of 1.1 ml of EtI (7.1 mmol) in 10 ml THF, at −10° C. After 2 hours, the THF was removed under vacuum, and Et2O was added. The thus obtained etcher solution was washed 3 times with a saturated solution of NaHCO3 and 3 times with a saturated aqueous solution of NaCl. After drying over MgSO4, 1.46 g of 1,2-bis(1-ethyl-2-indenyl)ethane was isolated, in the form of a yellow oil. 1H NMR and GC showed that it consisted of the three possible double bond isomers.

Workup

additionTo the obtained mixture was added, by means of a cannula
customat −10° C
waitAfter 2 hours
customthe THF was removed under vacuum, and Et2O
additionwas added
washThe thus obtained etcher solution was washed 3 times with a saturated solution of NaHCO3 and 3 times with a saturated aqueous solution of NaCl
dry with materialAfter drying over MgSO4

Sources & evidence

ORD record: ord-0cb16bd7ab0e407f8f1ad42349efd91c
Source dataset: uspto-grants-2004_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06673880B2

Reaction notes

Loading…