Diethyl Ether → HCID 19373357, compound

HRID 1197329Notes

Reaction equation

HRID 1197329 reaction equation
C([Li])CCC.Br[C:7](Br)=[CH:8][CH:9]1[CH2:14][CH2:13][CH:12]([C:15]23[O:22][CH2:21][C:18]([CH2:23][CH2:24][CH3:25])([CH2:19][O:20]2)[CH2:17][O:16]3)[CH2:11][CH2:10]1.CCOCC>CCCCCC.O1CCCC1>[C:8]([CH:9]1[CH2:10][CH2:11][CH:12]([C:15]23[O:16][CH2:17][C:18]([CH2:23][CH2:24][CH3:25])([CH2:19][O:20]2)[CH2:21][O:22]3)[CH2:13][CH2:14]1)#[CH:7]

Participants

6

Reactant 3

HCID 3283Diethyl EtherHCID 19373371HCID 19373371, compoundHCID 178418339Butyllithium

Product 1

HCID 19373357HCID 19373357, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

n-Butyllithium (1.6 ml of a 1.1M solution in hexane) was added at -70° C. to a solution of 1-[4-(2,2-dibromovinyl)cyclohexyl]-4-propyl-2,6,7-trioxabicyclo[2.2.2]octane (0.25 g) in dry tetrahydrofuran (5 ml) under a stream of nitrogen. After warming to room temperature over 2 hours ether (~25 ml) was added. The ethereal solution was washed with brine and dried over anhydrous magnesium sulphate. The solvent was removed in vacuo and the residue was purified by column chromatography on alumina eluting with 3:7 dichloromethane:hexane saturated with ammonia. 1-(4-Ethynylcyclohexyl)-4-propyl-2,6,7-trioxabicyclo[2.2.2]octane was obtained as a colourless oil (0.13 g).

Workup

  1. additionwas added
  2. washThe ethereal solution was washed with brine
  3. dry with materialdried over anhydrous magnesium sulphate
  4. customThe solvent was removed in vacuo
  5. customthe residue was purified by column chromatography on alumina eluting with 3:7 dichloromethane

Sources & evidence

ORD record
ord-231ee0516455474c8bfe27f9a92c0e88
Source dataset
uspto-grants-1992_05
Patent number
US05116862

Reaction notes

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