Ethyl Bromide → HCID 12773961, compound

HRID 848618Notes

Reaction equation

HRID 848618 reaction equation
[Mg].C(Br)C.[O:5]1[CH2:10][CH2:9][CH2:8][CH2:7][CH:6]1[O:11][CH2:12][C:13]#[CH:14].Br[CH2:16]/[CH:17]=[CH:18]/[CH2:19][CH2:20][CH3:21]>O1CCCC1.Cl>[O:5]1[CH2:10][CH2:9][CH2:8][CH2:7][CH:6]1[O:11][CH2:12][C:13]#[C:14][CH2:16]/[CH:17]=[CH:18]/[CH2:19][CH2:20][CH3:21]

Participants

7

Reactant 4

HCID 6332Ethyl BromideHCID 98609Tetrahydro-2-(2-propynyloxy)-2H-pyranHCID 5462224MagnesiumHCID 103747532-Hexenyl bromide

Product 1

HCID 12773961HCID 12773961, compoundYield 73.3%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 8028TetrahydrofuranSolvent3×

Procedure

To a solution of magnesium metal (8.6 g) in dry tetrahydrofuran (100 ml) was added dropwise ethyl bromide (39 g) in a nitrogen atmosphere at ambient temperature. After the mixture was stirred for an hour at the same temperature, to the mixture was added dropwise a solution of 3-(2-tetrahydropyranyloxy)-1-propyne (50 g) in dry tetrahydrofuran (75 ml) and cuprous cyanide (20 mg). The reaction mixture was stirred for 30 minutes at ambient temperature. To the mixture was added with stirring a solution of 1-bromo-trans-2-hexene (58 g) in dry tetrahydrofuran (75 ml) under ice-cooling. The reaction mixture was stirred for 30 minutes at ambient temperature and concentrated under reduced pressure to give a residue, which was dissolved in diluted hydrochloric acid and extracted with ether. The extract was washed with water, dried over anhydrous magnesium sulfate and concentrated under reduced pressure to give a yellowish oily residue, which was distilled under reduced pressure to give colorless oily 1-(2-tetrahydropyranyloxy)-trans-5-nonen-2-yne (58 g).

Workup

  1. stirringThe reaction mixture was stirred for 30 minutes at ambient temperature
  2. additionTo the mixture was added
  3. temperaturecooling
  4. stirringThe reaction mixture was stirred for 30 minutes at ambient temperature
  5. concentrationconcentrated under reduced pressure
  6. customto give a residue, which
  7. extractionextracted with ether
  8. washThe extract was washed with water
  9. dry with materialdried over anhydrous magnesium sulfate
  10. concentrationconcentrated under reduced pressure
  11. customto give a yellowish oily residue, which
  12. distillationwas distilled under reduced pressure

Sources & evidence

ORD record
ord-77e7b4971bf14f21b1ce29c5b3231860
Source dataset
uspto-grants-1981_10
Patent number
US04297096

Reaction notes

Loading…