1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 11402394, compound

HRID 2250306Notes

Reaction equation

HRID 2250306 reaction equation
Br[C:2]1([CH3:19])[O:6][C:5]([CH3:17])([C:7]23[CH2:16][CH:11]4[CH2:12][CH:13]([CH2:15][CH:9]([CH2:10]4)[CH2:8]2)[CH2:14]3)[O:4][C:3]1=[O:18].C1CCN2C(=NCCC2)CC1>C(OC(C)C)(C)C>[CH2:19]=[C:2]1[O:6][C:5]([C:7]23[CH2:14][CH:13]4[CH2:15][CH:9]([CH2:10][CH:11]([CH2:12]4)[CH2:16]2)[CH2:8]3)([CH3:17])[O:4][C:3]1=[O:18]

Participants

4

Reactant 2

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 11267468HCID 11267468, compound

Product 1

HCID 11402394HCID 11402394, compoundYield 14%

Reagents, catalysts & solvents 1

HCID 7914Diisopropyl EtherSolvent2×

Procedure

16.5 g (0.05 mol) of 5-bromo-2,5-dimethyl-2-(1-adamantyl)-1,3-dioxolan-4-one was placed in a 500 ml egg-plant type flask, and 200 g of isopropyl ether was added thereto and dissolved therein. While cooling with a refrigerant of −10° C., 9.1 g (0.06 mol) of 1,8-diazabicyclo[5.4.0]-7-undecene diluted with 20 g of isopropyl ether was added by drops into the solution over 1 hour, followed by stirring at room temperature for 2 hours. After completion of the stirring, the reaction solution was analyzed. As a result, it was found that the reaction solution contained only 1.7 g of 5-methylene-2-(1-adamantyl)-2-methyl-1,3-dioxolan-4-one (yield: 14%) and that 80% of the raw materials was decomposed into adamantyl methyl ketone.

Workup

  1. dissolutiondissolved
  2. additionwas added by drops into the solution over 1 hour

Sources & evidence

ORD record
ord-f092cb48c07648cb8411466b8a520628
Source dataset
uspto-grants-2008_01
Patent number
US07316884B2

Reaction notes

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