Propylethinylcarbinol → HCID 20226190, compound

HRID 1248875Notes

Reaction equation

HRID 1248875 reaction equation
[CH:1]#[C:2][CH:3]([OH:7])[CH2:4][CH2:5][CH3:6].C([Li])CCC.[CH2:13]([C:15]1([CH3:23])[CH2:20][CH2:19][CH2:18][CH:17]([CH3:21])[C:16]1=[O:22])[CH3:14]>O1CCCC1.CCCCCC>[CH2:13]([C:15]1([CH3:23])[CH2:20][CH2:19][CH2:18][CH:17]([CH3:21])[C:16]1([C:1]#[C:2][CH:3]([OH:7])[CH2:4][CH2:5][CH3:6])[OH:22])[CH3:14]

Participants

6

Reactant 3

HCID 7746PropylethinylcarbinolHCID 21720218HCID 21720218, compoundHCID 178418339Butyllithium

Product 1

HCID 20226190HCID 20226190, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

40.2 G (0.41M) of 1-hexyn-3-ol in 200 ml of anhydrous tetrahydrofurane (THF) have been placed in a three-necked reaction vessel and cooled to -70°. At this temperature there were added under stirring 390 ml (0.91M) of a 15% solution of butyl-lithium in hexane and the temperature was then raised to about 20° within one night. A solution of 40 g (0.26M) of 2-ethyl-2,6-dimethylcyclohexanone in 90 ml of THF-75/25 isomeric mixture of the following compounds ##STR15## was added dropwise to the reaction mixture cooled again to -70°. After having been kept under stirring for 3 h at -70° and overnight at room temperature, the mixture was poured onto ice, extracted with ether, washed with brine until neutrality, dried over Na2SO4, filtered and concentrated.

Workup

  1. temperaturecooled to -70°
  2. additionAt this temperature there were added
  3. temperaturethe temperature was then raised to about 20° within one night
  4. additionwas added dropwise to the reaction mixture
  5. temperaturecooled again to -70°
  6. additionthe mixture was poured onto ice
  7. extractionextracted with ether
  8. washwashed with brine until neutrality
  9. dry with materialdried over Na2SO4
  10. filtrationfiltered
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-084c2e2dcff343baba63e1b6f2b72ef8
Source dataset
uspto-grants-1986_12
Patent number
US04626602

Reaction notes

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