Hydrochloric Acid → HCID 178444487, compound

HRID 1491518Notes

Reaction equation

HRID 1491518 reaction equation
[CH3:1][Si:2]([CH3:14])([CH3:13])[O:3][CH2:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]#[CH:12])=[CH:7][CH:6]=1.[CH2:15]([CH:20]1[CH2:25][CH2:24][CH:23]([CH2:26][CH:27]=[O:28])[CH2:22][CH2:21]1)[CH2:16][CH2:17][CH2:18][CH3:19].Cl>C1COCC1>[CH3:1][Si:2]([CH3:13])([CH3:14])[O:3][CH2:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]#[C:12][CH:27]([OH:28])[CH2:26][C@H:23]2[CH2:24][CH2:25][C@H:20]([CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[CH2:21][CH2:22]2)=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 139990854-PentylcyclohexaneacetaldehydeHCID 189528534-Trimethylsilyloxymethylphenylacetylene

Product 1

HCID 178444487HCID 178444487, compoundYield 62.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

4-Trimethylsilyloxymethylphenylacetylene (20 mmol) was dissolved in THF (20 ml), followed by dropwise adding n-butyllithium-hexane solution (1.61M, 12.4 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 (4.0 g) in THF (10 ml), raising the temperature of the reaction solution up to room temperature after completion of the dropwise addition, stirring for 5 hours, adding dilute hydrochloric acid (5 ml) to the resulting raw solution, extracting with ethyl acetate (150 ml), washing the organic phase with water, drying over anhydrous MgSO4, concentrating under reduced pressure to obtain a brown oil, and recrystallizing it from a mixed solution of ethyl acetate-heptane, to obtain 1-(4-trimethylsilyloxymethylphenyl)-4-(trans-4-pentylcyclohexyl)-1-butyn-3-ol (white crystals) (5.0 g).

Workup

  1. temperaturecooling
  2. stirringstirring the reaction solution under ice-
  3. temperaturecooling for 30 minutes
  4. additionafter completion of the dropwise addition
  5. stirringstirring for 5 hours
  6. extractionextracting with ethyl acetate (150 ml)
  7. washwashing the organic phase with water
  8. dry with materialdrying over anhydrous MgSO4
  9. concentrationconcentrating under reduced pressure
  10. customto obtain a brown oil
  11. customrecrystallizing it from a mixed solution of ethyl acetate-heptane

Sources & evidence

ORD record
ord-73be2e9a4f564b2899ce82cedd3902f9
Source dataset
uspto-grants-1994_12
Patent number
US05370819

Reaction notes

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