Tetrahydrofuran → HCID 18364505, compound

HRID 380260Notes

Reaction equation

HRID 380260 reaction equation
[CH:1]1([CH:8]2[CH2:13][CH2:12][C:11](=[O:14])[CH2:10][CH2:9]2)[CH2:6][CH2:5][C:4](=[O:7])[CH2:3][CH2:2]1.O.O.O.[F-].[CH2:19]([N+](CCCC)(CCCC)CCCC)[CH2:20]CC.[F-].[K+].[CH2:38]1COC[CH2:39]1>CO>[C:19]([C:4]1([OH:7])[CH2:5][CH2:6][CH:1]([CH:8]2[CH2:9][CH2:10][C:11]([C:38]#[CH:39])([OH:14])[CH2:12][CH2:13]2)[CH2:2][CH2:3]1)#[CH:20]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 2648254,4'-BicyclohexanoneHCID 522689Potassium FluorideHCID 11726816Tetrabutylammonium Fluoride Trihydrate

Product 1

HCID 18364505HCID 18364505, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

30.00 g of bicyclohexyl-4,4′-dione and 3.89 g of tetrabutylammonium fluoride trihydrate are dissolved in 350 ml of THF, and 30.33 g of trimethylsiylacetylene are added dropwise at RT. The reaction mixture is stirred for 2 days, a suspension of 44.86 g of potassium fluoride in 160 ml of methanol is subsequently added, and the mixture is stirred for a further 3 days. Conventional work-up gives 4,4′-diethynylbicyclohexyl-4,4′-diol.

Workup

  1. addition30.33 g of trimethylsiylacetylene are added dropwise at RT
  2. additionis subsequently added
  3. stirringthe mixture is stirred for a further 3 days

Sources & evidence

ORD record
ord-46232f58851b4229a30c699cce7a541e
Source dataset
uspto-grants-2001_10
Patent number
US06303194B1

Reaction notes

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