Hydrochloric Acid → HCID 18952790, compound

HRID 1491519Notes

Reaction equation

HRID 1491519 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]#[CH:9])=[CH:4][CH:3]=1.[CH2:10]([CH:15]1[CH2:20][CH2:19][CH:18]([CH2:21][CH:22]=[O:23])[CH2:17][CH2:16]1)[CH2:11][CH2:12][CH2:13][CH3:14].Cl>C1COCC1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]#[C:9][CH:22]([OH:23])[CH2:21][CH:18]2[CH2:19][CH2:20][CH:15]([CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])[CH2:16][CH2:17]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 5226271-Ethynyl-4-fluorobenzeneHCID 139990854-Pentylcyclohexaneacetaldehyde

Product 1

HCID 18952790HCID 18952790, compoundYield 95.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

4-Fluorophenylacetylene (1.3 g) was dissolved in THF (20 ml), followed by dropwise adding a n-butyllithium-hexane solution (1.61M, 0.62 ml) while stirring the above solution under ice-cooling, stirring the reaction solution under ice-cooling for 30 minutes, dropwise adding a solution of 2-(4-pentylcyclohexyl)acetaldehyde (1.5 g) in THF (10 ml), raising the temperature of the reaction solution up to room temperature after completion of the dropwise addition, stirring the mixture for 5 hours, adding dilute hydrochloric acid (5 ml) to the resulting raw solution, extracting with ethyl acetate (50 ml), washing the organic layer with water, drying over anhydrous MgSO4, concentrating under reduced pressure to obtain a brown oil, and recrystallizing this oil from a mixed solution of ethyl acetate-heptane, to obtain 1-(4-fluorophenyl)-4-(4-pentylcyclohexyl)-1-butyn-3-ol (white crystal) (2.3 g) .

Workup

  1. additionby dropwise adding a n-butyllithium-hexane solution (1.61M, 0.62 ml)
  2. temperaturecooling
  3. stirringstirring the reaction solution under ice-
  4. temperaturecooling for 30 minutes
  5. additionafter completion of the dropwise addition
  6. stirringstirring the mixture for 5 hours
  7. extractionextracting with ethyl acetate (50 ml)
  8. washwashing the organic layer with water
  9. dry with materialdrying over anhydrous MgSO4
  10. concentrationconcentrating under reduced pressure
  11. customto obtain a brown oil
  12. customrecrystallizing this oil from a mixed solution of ethyl acetate-heptane

Sources & evidence

ORD record
ord-5db81fd6d6be40399384a076d37c7964
Source dataset
uspto-grants-1994_12
Patent number
US05370819

Reaction notes

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