Hydrochloric Acid → 1-(4-Trimethylsilyloxycyclohexyl)-4-(4-pentylcyclohexyl)-1-butyn-3-ol

HRID 1491517Notes

Reaction equation

HRID 1491517 reaction equation
[CH3:1][Si:2]([CH3:13])([CH3:12])[O:3][CH:4]1[CH2:9][CH2:8][CH:7]([C:10]#[CH:11])[CH2:6][CH2:5]1.[CH2:14]([CH:19]1[CH2:24][CH2:23][CH:22]([CH2:25][CH:26]=[O:27])[CH2:21][CH2:20]1)[CH2:15][CH2:16][CH2:17][CH3:18].Cl>C1COCC1>[CH3:1][Si:2]([CH3:12])([CH3:13])[O:3][CH:4]1[CH2:9][CH2:8][CH:7]([C:10]#[C:11][CH:26]([OH:27])[CH2:25][CH:22]2[CH2:23][CH2:24][CH:19]([CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[CH2:20][CH2:21]2)[CH2:6][CH2:5]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 139990854-PentylcyclohexaneacetaldehydeHCID 189527924-Trimethylsilyloxycyclohexylacetylene

Product 1

HCID 189528661-(4-Trimethylsilyloxycyclohexyl)-4-(4-pentylcyclohexyl)-1-butyn-3-olYield 63.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

4-Trimethylsilyloxycyclohexylacetylene (20 mmol) was dissolved in THF (20 ml), followed by dropwise adding a 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 it for 5 hours, adding dilute hydrochloric acid (5 ml) to the resulting raw solution, extracting the mixture with ethyl acetate (150 ml), washing the organic phase with water, drying over anhydrous MgSO4, concentrating under reduced pressure to obtain a brown oil, which is recrystallized from a mixed solution of ethyl acetate-heptane, to obtain 1-(4-trimethylsilyloxycyclohexyl)-4-(4-pentylcyclohexyl)-1-butyn-3-ol (5.0 g) (white crystal).

Workup

  1. additionby dropwise adding a n-butyllithium-hexane solution (1.61M, 12.4 ml)
  2. stirringstirring the reaction solution under ice cooling for 30 minutes
  3. additionafter completion of the dropwise addition
  4. stirringstirring it for 5 hours
  5. extractionextracting the mixture with ethyl acetate (150 ml)
  6. washwashing the organic phase with water
  7. dry with materialdrying over anhydrous MgSO4
  8. concentrationconcentrating under reduced pressure
  9. customto obtain a brown oil, which
  10. customis recrystallized from a mixed solution of ethyl acetate-heptane

Sources & evidence

ORD record
ord-4eca8499336243f7a907755a7d8bd002
Source dataset
uspto-grants-1994_12
Patent number
US05370819

Reaction notes

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