Ammonium Chloride → HCID 23050507, compound

HRID 1651787Notes

Reaction equation

HRID 1651787 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][O:16][C:17]1[CH:24]=[CH:23][C:20]([CH:21]=[O:22])=[CH:19][CH:18]=1.[Cl-].[NH4+]>O1CCCC1>[CH2:1]([O:3][CH:4]([O:6][CH2:7][C:8]#[C:9][CH:21]([C:20]1[CH:23]=[CH:24][C:17]([O:16][CH3:15])=[CH:18][CH:19]=1)[OH:22])[CH3:5])[CH3:2]

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 312444-MethoxybenzaldehydeHCID 867741-Propyne, 3-(1-ethoxyethoxy)-HCID 178418339Butyllithium

Product 1

HCID 23050507HCID 23050507, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 6 g (47 mmol) of 1-(1-ethoxyethoxy)-2-propyne in 100 ml of tetrahydrofuran was treated at -78° under argon with 29.2 ml of n-butyllithium (1.6M in hexane). The mixture was stirred at -40° for 30 minutes and then a solution of 5.7 ml (47 mmol) of 4-methoxybenzaldehyde in 41 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 80 ml of saturated ammonium chloride solution. The aqueous phase was extracted twice with ethyl acetate. 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 flash chromatography on 500 g of silica gel (elution agent ether/hexane 1:1). There was obtained 4-(1-ethoxyethoxy)-1-(4-methoxyphenyl)-2-butyn-1-ol as an oil.

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 ethyl acetate
  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 flash chromatography on 500 g of silica gel (elution agent ether/hexane 1:1)

Sources & evidence

ORD record
ord-160a1059fd2548c7994198248e66d006
Source dataset
uspto-grants-1990_05
Patent number
US04929741

Reaction notes

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