Ethylamine → 2,4-Heptadiyn-1-ol, 6-methoxy-6-methyl-

HRID 1464783Notes

Reaction equation

HRID 1464783 reaction equation
C(N)C.Cl.NO.[CH2:7]([OH:10])[C:8]#[CH:9].Br[C:12]#[C:13][C:14]([O:17][CH3:18])([CH3:16])[CH3:15]>CO.[Cu]Cl>[CH3:18][O:17][C:14]([CH3:16])([CH3:15])[C:13]#[C:12][C:9]#[C:8][CH2:7][OH:10]

Participants

7

Reactant 4

HCID 6341EthylamineHCID 7859Propargyl alcoholHCID 443297Hydroxyamine hydrochlorideHCID 103522261-Butyne, 1-bromo-3-methoxy-3-methyl-

Product 1

HCID 99894232,4-Heptadiyn-1-ol, 6-methoxy-6-methyl-Yield 89.6%

Reagents, catalysts & solvents 2

HCID 62652Cuprous chlorideCatalystHCID 887MethanolSolvent2×

Procedure

200 ml of a 70% aqueous solution of ethyamine, 1 g of copper(I) chloride, 5 g of hydroxylamine hydrochloride and 25 g of propargyl alcohol were dissolved in 500 ml of methanol, and with ice cooling and stirring, a methanol solution (100 ml) of 74 g of 1-bromo-3-methoxy-3-methyl-1-butyne was added. The mixture was stirred at room temperature for 1 hour, and then the solvent was evaporated. Water and ethyl acetate were added, and the insoluble material was removed by filtration. The organic layer separated was worked up in a customary manner, and the product was purified by vacuum distillation ( b.p. -97° C. / 2 mmHg ) to give 57 g of the captioned compound as a colorless oil.

Workup

  1. stirringThe mixture was stirred at room temperature for 1 hour
  2. customthe solvent was evaporated
  3. additionWater and ethyl acetate were added
  4. customthe insoluble material was removed by filtration
  5. customThe organic layer separated
  6. distillationthe product was purified by vacuum distillation ( b.p. -97° C. / 2 mmHg )

Sources & evidence

ORD record
ord-1a16649ea5e848ea93612e0392f12700
Source dataset
uspto-grants-1994_04
Patent number
US05306728

Reaction notes

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