4-Methylbenzaldehyde → HCID 23050505, compound

HRID 1651784Notes

Reaction equation

HRID 1651784 reaction equation
[CH2:1]([O:3][CH:4]([O:6][CH2:7][C:8]#[CH:9])[CH3:5])[CH3:2].C([Li])CCC.[CH3:15][C:16]1[CH:23]=[CH:22][C:19]([CH:20]=[O:21])=[CH:18][CH:17]=1.[Cl-].[NH4+]>O1CCCC1>[CH2:1]([O:3][CH:4]([O:6][CH2:7][C:8]#[C:9][CH:20]([C:19]1[CH:22]=[CH:23][C:16]([CH3:15])=[CH:17][CH:18]=1)[OH:21])[CH3:5])[CH3:2]

Participants

6

Reactant 4

HCID 77254-MethylbenzaldehydeHCID 25517Ammonium ChlorideHCID 867741-Propyne, 3-(1-ethoxyethoxy)-HCID 178418339Butyllithium

Product 1

HCID 23050505HCID 23050505, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 5 g (33 mmol) of 1-(1-ethoxyethoxy)-2-propyne in 84 ml of tetrahydrofuran was treated at -78° under argon with 24.4 ml of n-butyllithium (1.6M in hexane). The mixture was stirred at -40° for 30 minutes and then a solution of 4.6 ml (33 mmol) of 4-methylbenzaldehyde in 34 ml of tetrahydrofuran was added within 10 minutes. The reaction mixture was warmed to 0° , stirred at 0° for a further 1 hour and then treated with 60 ml of saturated ammonium chloride solution. The aqueous phase was extracted twice with ether. The combined organic phases were washed in succession with saturated sodium chloride solution and with water, dried over magnesium sulphate and concentrated. The residue was purified by chromatography on 500 g of silica gel (elution agent ether/hexane 1:1). There was obtained 4-(1-ethoxyethoxy)-1-(4-methylphenyl)-2 -butyn-1-ol.

Workup

  1. temperatureThe reaction mixture was warmed to 0°
  2. stirringstirred at 0° for a further 1 hour
  3. extractionThe aqueous phase was extracted twice with ether
  4. washThe combined organic phases were washed in succession with saturated sodium chloride solution and with water
  5. dry with materialdried over magnesium sulphate
  6. concentrationconcentrated
  7. customThe residue was purified by chromatography on 500 g of silica gel (elution agent ether/hexane 1:1)

Sources & evidence

ORD record
ord-85886e1290a14bd0a9eda1a8870a7ace
Source dataset
uspto-grants-1990_05
Patent number
US04929741

Reaction notes

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