Water → 3-[4-(3-Dimethylaminopropoxy)-phenyl]-3-hydroxy-1-propyne

HRID 428668Notes

Reaction equation

HRID 428668 reaction equation
[CH3:1][N:2]([CH3:15])[CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:14]=[CH:13][C:10]([CH:11]=[O:12])=[CH:9][CH:8]=1.[C:16]([Mg]Cl)#[CH:17].O>O1CCCC1>[CH3:15][N:2]([CH3:1])[CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:8]=[CH:9][C:10]([CH:11]([OH:12])[C:16]#[CH:17])=[CH:13][CH:14]=1

Participants

5

Reactant 3

HCID 962WaterHCID 5469324-[3-(Dimethylamino)propoxy]benzaldehydeHCID 178462451HCID 178462451, compound

Product 1

HCID 183592823-[4-(3-Dimethylaminopropoxy)-phenyl]-3-hydroxy-1-propyne

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-(3-dimethylaminopropoxy)benzaldehyde (0.83 g, 4 mmol) (Aldrich) in dry tetrahydrofuran (30 mL) under argon at room temperature was added ethynylmagnesium chloride (5 mmmol, 10 mL, 0.5M solution in tetrahydrofuran) (Aldrich) dropwise. The resulting solution was stirred for 1.5 h at which time 100 mL water was added, and the THF was removed in vacuo. The product was extracted with ethyl acetate (3×50 mL) and the combined organic layers were dried over magnesium sulfate and concentrated in vacuo to give clean 3-[4-(3-dimethylaminopropoxy)-phenyl]-3-hydroxy-1-propyne which was used directly, without further purification. (Yield 831 mg, 89%)

Workup

  1. additionwas added
  2. customthe THF was removed in vacuo
  3. extractionThe product was extracted with ethyl acetate (3×50 mL)
  4. dry with materialthe combined organic layers were dried over magnesium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-711d3a560da448f6892348fd66991d2a
Source dataset
uspto-grants-2001_11
Patent number
US06313310B1

Reaction notes

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