Ammonium Chloride → HCID 23050514, compound

HRID 1651785Notes

Reaction equation

HRID 1651785 reaction equation
[CH2:1]([O:3][CH:4]([O:6][CH2:7][C:8]#[CH:9])[CH3:5])[CH3:2].C([Li])CCC.[F: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]([F:15])=[CH:17][CH:18]=1)[OH:21])[CH3:5])[CH3:2]

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 680234-FluorobenzaldehydeHCID 867741-Propyne, 3-(1-ethoxyethoxy)-HCID 178418339Butyllithium

Product 1

HCID 23050514HCID 23050514, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 8 g (62.4 mmol) of 1 (1-ethoxyethoxy)-2-propyne in 134 ml of tetrahydrofuran was treated at -78° under argon with 39 ml of n-butyllithium (1.6M in hexane). The mixture was stirred at -40° for 30 minutes and then a solution of 6.6 ml (62 mmol) of 4-fluorobenzaldehyde in 54 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 100 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 chromatography on 600 g of silica gel (elution agent ether/hexane 1:1). There was obtained 4-(1-ethoxyethoxy)-1-(4-fluorophenyl)-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 chromatography on 600 g of silica gel (elution agent ether/hexane 1:1)

Sources & evidence

ORD record
ord-5605d4c22b6247859ad721b686ae24af
Source dataset
uspto-grants-1990_05
Patent number
US04929741

Reaction notes

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