Diethyl Ether → 7-Methoxyhept-1-yne

HRID 1511871Notes

Reaction equation

HRID 1511871 reaction equation
[H-].[Na+].CI.[CH2:5]([OH:12])[CH2:6][CH2:7][CH2:8][CH2:9][C:10]#[CH:11].[CH3:13]COCC>CN(C=O)C.O>[CH3:13][O:12][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10]#[CH:11]

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 6328Methyl iodide2×HCID 24758Sodium hydride3×HCID 110078496-Heptyn-1-ol

Product 1

HCID 575547897-Methoxyhept-1-yneYield 61.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

To a slurry of sodium hydride (7.86 g, 197 mmol) in DMF (100 mL) was added methyl iodide (12.29 mL, 197 mmol) followed by a solution of hept-6-yn-1-ol (24.5 g, 197 mmol) in DMF (50 mL). Following the addition the reaction was monitored by TLC. After 2 h additional methyl iodide (6 mL, 50 mmol) was added followed by sodium hydride (1 g, 25 mmol) portions. At 1 h intervals additional sodium hydride (1 g, 25 mmol) portions was added until no alcohol remained as indicated by TLC. Et2O (50 mL) and water (100 mL) was added to the reaction mixture and the layers were separated. The organic layer was washed with brine, dried using Na2SO4, filtered and distilled (145-155° C.) to provide 7-methoxyhept-1-yne (18 g, 121 mmol, 61.7% yield) as a colorless oil.

Workup

  1. additionthe addition the reaction
  2. customthe layers were separated
  3. washThe organic layer was washed with brine
  4. customdried
  5. filtrationfiltered
  6. distillationdistilled (145-155° C.)

Sources & evidence

ORD record
ord-2770c457b06c4249af250c83c3e317f7
Source dataset
uspto-grants-2012_07
Patent number
US08217027B2

Reaction notes

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