Diethyl Ether → HCID 19917043, compound

HRID 1756171Notes

Reaction equation

HRID 1756171 reaction equation
[C:1]([C:5]#[CH:6])([CH3:4])([CH3:3])[CH3:2].Br[CH2:8][CH2:9][CH2:10][O:11][CH:12]1[CH2:17][CH2:16][CH2:15][CH2:14][O:13]1.C(OCC)C>O1CCCC1>[CH3:2][C:1]([CH3:4])([CH3:3])[C:5]#[C:6][CH2:8][CH2:9][CH2:10][O:11][CH:12]1[CH2:17][CH2:16][CH2:15][CH2:14][O:13]1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 135123,3-Dimethyl-1-butyneHCID 27779882-(3-Bromopropoxy)tetrahydro-2H-pyran

Product 1

HCID 19917043HCID 19917043, compoundYield 40.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

0.81 g of tert-butylacetylene was dissolved in 19 ml of tetrahydrofuran, and 6.1 ml of a 0.55M n-butyllithium-hexane solution was added dropwise with stirring at -78° C. After the mixture was stirred at this temperature for 1 hour, 2.2 g of 3-bromo-1-(2-tetrahydropyranyloxy)propane was added. The solution was warmed to the room temperature, and then heated at 80° C. with stirring for 8 hours. The reaction mixture was poured into the ice water, and ethyl ether was added. The organic layer separated was worked up in a customary manner, and the product was purified by silica gel column chromatography [hexane/ethyl acetate=20/1] to give 0.90 g of 6,6-dimethyl-1-(2-tetrahydropyranyloxy)- 4-heptyne.

Workup

  1. addition6.1 ml of a 0.55M n-butyllithium-hexane solution was added dropwise
  2. stirringAfter the mixture was stirred at this temperature for 1 hour
  3. temperatureThe solution was warmed to the room temperature
  4. temperatureheated at 80° C.
  5. stirringwith stirring for 8 hours
  6. additionwas added
  7. customThe organic layer separated
  8. customthe product was purified by silica gel column chromatography [hexane/ethyl acetate=20/1]

Sources & evidence

ORD record
ord-01492cfed83149f5a46316a14f5df21c
Source dataset
uspto-grants-1995_08
Patent number
US05439932

Reaction notes

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