1,3-Dioxolane, 2-(bromomethyl)- → HCID 20229697, compound

HRID 2291140Notes

Reaction equation

HRID 2291140 reaction equation
[CH:1]12[CH2:7][CH:4]([CH2:5][CH2:6]1)[CH2:3][CH:2]2[C:8]#[N:9].C([N-]C(C)C)(C)C.[Li+].Br[CH2:19][CH:20]1[O:24][CH2:23][CH2:22][O:21]1>C(OCC)(=O)C.C1CCCCC1>[C:8]([C:2]1([CH2:19][CH:20]2[O:24][CH2:23][CH2:22][O:21]2)[CH2:3][CH:4]2[CH2:7][CH:1]1[CH2:6][CH2:5]2)#[N:9]

Participants

5

Reactant 3

HCID 780681,3-Dioxolane, 2-(bromomethyl)-HCID 1022312-NorbornanecarbonitrileHCID 2724682Lithium diisopropylamide

Product 1

HCID 20229697HCID 20229697, compoundYield 92.1%

Reagents, catalysts & solvents 1

HCID 21867204Cyclohexane ethylacetateSolvent

Procedure

7.2 g of norbornane-2-carbonitrile are reacted with 60 mmoles of lithium diisopropylamide (prepared from 8.2 ml of diisopropylamine and 40 ml of n-butyllithium) and with 7 g of 2-bromomethyl-1,3-dioxolane in analogy to Example 1a. After chromatography on silica gel with ethyl acetate/cyclohexane (1:6) as the mobile phase, 8.0 g of the title compound are obtained as an oil.

Sources & evidence

ORD record
ord-7be61942fbad4fddb4466625c35805d7
Source dataset
uspto-grants-1986_10
Patent number
US04620012

Reaction notes

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