Propargyl bromide → 4-[(2-Propynyloxy)methyl]benzyl alcohol

HRID 1891916Notes

Reaction equation

HRID 1891916 reaction equation
[H-].[Na+].O1C[CH2:6][CH2:5][CH2:4]1.[C:8]1([CH2:16][OH:17])[CH:13]=[CH:12][C:11]([CH2:14][OH:15])=[CH:10][CH:9]=1.C(Br)C#C>O.CN(C)C=O>[CH2:6]([O:15][CH2:14][C:11]1[CH:12]=[CH:13][C:8]([CH2:16][OH:17])=[CH:9][CH:10]=1)[C:5]#[CH:4]

Participants

7

Reactant 4

HCID 7842Propargyl bromideHCID 8028TetrahydrofuranHCID 115061,4-BenzenedimethanolHCID 24758Sodium hydride

Product 1

HCID 545201314-[(2-Propynyloxy)methyl]benzyl alcoholYield 58%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a mixture of sodium hydride (400 mg, 8.4 mmol, 50% in oil) and tetrahydrofuran (30 mL) was added 1,4-benzenedimethanol (2.3 g, 17 mmol) at 0° C., and then N,N-dimethylformamide (30 mL) was added. The reaction mixture was stirred at room temperature for 10 minutes, after which propargyl bromide (1.0 g, 8.4 mmol) was added dropwise to the reaction mixture at 0° C. The reaction mixture was stirred at room temperature for 1 hour, after which water was added to the reaction mixture, which was extracted with ethyl acetate. The organic layer was washed and saturated aqueous sodium chloride, and was concentrated under a reduced pressure. The residue thus obtained was purified by NH silica gel column chromatography (heptane:ethyl acetate=3:2) to obtain the title compound (860 mg, 58%).

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 1 hour
  2. extractionwas extracted with ethyl acetate
  3. washThe organic layer was washed
  4. concentrationsaturated aqueous sodium chloride, and was concentrated under a reduced pressure
  5. customThe residue thus obtained
  6. customwas purified by NH silica gel column chromatography (heptane:ethyl acetate=3:2)

Sources & evidence

ORD record
ord-b2c06bf3852446368d5453e90de6955c
Source dataset
uspto-grants-2013_08
Patent number
US08507530B2

Reaction notes

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