Diethyl Ether → HCID 19373357, compound

HRID 129278Notes

Reaction equation

HRID 129278 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-7d2be41631434a64a26a12d2d7fbc039
Source dataset
uspto-grants-1995_11
Patent number
US05466710

Reaction notes

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