Propargyl bromide → 3,6,9,12-Tetraoxapentadec-14-yn-1-ol

HRID 1408237Notes

Reaction equation

HRID 1408237 reaction equation
[H-].[Na+].[CH2:3]([OH:15])[CH2:4][O:5][CH2:6][CH2:7][O:8][CH2:9][CH2:10][O:11][CH2:12][CH2:13][OH:14].[CH2:16](Br)[C:17]#[CH:18]>C1COCC1>[CH2:13]([OH:14])[CH2:12][O:11][CH2:10][CH2:9][O:8][CH2:7][CH2:6][O:5][CH2:4][CH2:3][O:15][CH2:18][C:17]#[CH:16]

Participants

5

Reactant 3

HCID 7842Propargyl bromideHCID 8200Tetraethylene GlycolHCID 24758Sodium hydride

Product 1

HCID 159170603,6,9,12-Tetraoxapentadec-14-yn-1-olYield 51.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of sodium hydride (60% in oil, 740 mg, 18.5 mmol) in THF (50 mL) at 0° C. was added tetraethylene glycol (4.0 g, 20.6 mmol). After stirring for 15 minutes, propargyl bromide (80% in toluene, 2.00 mL, 18.0 mmol) was added slowly. The reaction was allowed to warm to RT and stirred 16 hours. Solids were removed by filtration and rinsed with MTBE (3×20 mL). The combined filtrates were concentrated and purified by flash chromatography on silica gel (EtOAc) to give 3,6,9,12-tetraoxapentadec-14-yn-1-ol (2.14 g).

Workup

  1. stirringstirred 16 hours
  2. customSolids were removed by filtration
  3. washrinsed with MTBE (3×20 mL)
  4. concentrationThe combined filtrates were concentrated
  5. custompurified by flash chromatography on silica gel (EtOAc)

Sources & evidence

ORD record
ord-373e620723ee488eb68c410b7f77af86
Source dataset
uspto-grants-2014_12
Patent number
US08916569B2

Reaction notes

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